Substituted benzoylcyclohexandiones

ABSTRACT

The invention relates to novel substituted benzoylcyclohexanediones of the general formula (I), 
                 
 
in which
     m, n, A, R 1 , R 2 , R 3 , R 4  and Z are each as defined in the description,
 
and also to processes for their preparation and to their use as herbicides.

This application is a 371 of PCT/EP99/04929 Jul. 13, 1999.

FIELD OF THE INVENTION

The invention relates to novel substituted benzoylcyclohexanediones, toprocesses for their preparation and to their use as herbicides.

BACKGROUND OF THE INVENTION

It is already known that certain substituted benzoylcyclohexanedioneshave herbicidal properties (cf. EP-A-090262, EP-A-135191, EP-A-186118,EP-A-186119. EP-A-186120, EP-A-319075, WO-A-96/26200, WO-A-97/46530,WO-A-99/07688). However, the activity of these compounds is not in allrespects satisfactory.

SUMMARY OF THE INVENTION

This invention, accordingly, provides the novel substitutedbenzoylcyclohexanediones of the general formula (I),

in which

-   m represents the numbers 0, 1, 2 or 3,-   n represents the numbers 0, 1, 2 or 3,-   A represents the single bond or represents alkanediyl (alkylene).-   R¹ represents hydrogen or represents in each case optionally    substituted alkyl or alkoxycarbonyl,-   R² represents optionally substituted alkyl, or together with R¹    represents alkanediyl (alkylene) where in this case m represents 1    and R¹ and R² are located at the same carbon atom (“geminal”) or at    two adjacent carbon atoms (“vicinal”),-   R³ represents hydrogen, nitro, cyano, carboxyl, carbamoyl,    thiocarbamoyl, halogen, or represents in each case optionally    substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,    alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,-   R⁴ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,    halogen, or represents in each case optionally substituted alkyl,    alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,    dialkylamino or dialkylamino-sulphonyl, and-   Z represents an optionally substituted 4- to 12-membered, saturated    or unsaturated, monocyclic or bicyclic, heterocyclic grouping which    contains 1 to 4 heteroatoms (up to 4 nitrogen atoms and, if    appropriate, —alternatively or additionally—one oxygen atom or one    sulphur atom, or one SO grouping or one SO₂ grouping), and which    additionally contains one to three oxo groups (C═O) and/or thioxo    groups (C═S) as components of the heterocycle,    including all possible tautomeric forms of the compounds of the    general formula (I) and the possible salts of the compounds of the    general formula (I).

In the definitions, the hydrocarbon chains, such as alkyl or alkanediylare in each case straight-chain or branched—including in combinationwith heteroatoms, such as in alkoxy.

In addition to the compounds of the general formula (I)— above—it is ineach case also possible for the corresponding tautomeric forms—shown inexemplary manner below—to be present.

Preferred substituents of the radicals listed in the formula shown aboveare illustrated below:

-   m preferably represents the numbers 0, 1 or 2.-   n preferably represents the numbers 0, 1 or 2.-   A preferably represents a single bond or represents alkanediyl    (alkylene) having 1 to 4 carbon atoms.-   R¹ preferably represents hydrogen, represents optionally halogen-,    C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or    C₁-C₄-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms or    represents alkoxycarbonyl having up to 6 carbon atoms.-   R² preferably represents optionally halogen-substituted alkyl having    1 to 6 carbon atoms, or together with R¹ represents alkanediyl    (alkylene) having 2 to 5 carbon atoms, where in this case m    represents 1 and R¹ and R² are located at the same carbon atom    (“geminal”) or at two adjacent carbon atoms (“vicinal”).-   R³ preferably represents hydrogen, nitro, cyano, carboxyl,    carbamoyl, thiocarbamoyl, halogen, represents in each case    optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,    C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl,    alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each    case up to 4 carbon atoms in the alkyl groups, or represents    alkylamino, dialkylamino or dialkylaminosulphonyl having in each    case up to 4 carbon atoms in the alkyl groups.-   R⁴ preferably represents nitro, cyano, carboxyl, carbamoyl,    thiocarbamoyl, halogen, represents in each case optionally halogen-,    C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or    C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,    alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon    atoms in the alkyl groups, or represents alkylamino, dialkylamino or    dialkylaminosulphonyl having in each case up to 4 carbon atoms in    the alkyl groups.-   Z preferably represents one of the heterocyclic groupings below    in which the bond drawn broken in each case denotes a single bond or    a double bond,-   Q represents oxygen or sulphur,-   R⁵ represents hydrogen, hydroxyl, mercapto, cyano, halogen,    represents in each case optionally cyano-, halogen-, C₁-C₄-alkoxy-,    C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or    C₁-C₄-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy,    alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having    in each case up to 6 carbon atoms in the alkyl groups, represents    propadienylthio, represents in each case optionally    halogen-substituted alkylamino or dialkylamino having in each case    up to 6 carbon atoms in the alkyl groups, represents in each case    optionally halogen-substituted alkenyl, alkinyl, alkenyloxy,    alkenylthio or alkenylamino having in each case up to 6 carbon atoms    in the alkenyl or alkinyl groups, represents in each case optionally    halogen-substituted cycloalkyl, cycloalkyloxy, cyclo-alkylthio,    cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy,    cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to    6 carbon atoms in the cycloalkyl groups and optionally up to 4    carbon atoms in the alkyl moiety, or represents in each case    optionally halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted    phenyl, phenyl-oxy, phenylthio, phenylamino, benzyl, benzyloxy,    benzylthio or benzylamino, represents pyrrolidino, piperidino or    morpholino, or—in the case that two adjacent radicals R⁵ and R⁵ are    located at a double bond—together with the adjacent radical R⁵ also    represents a benzo grouping, and-   R⁶ represents hydrogen, hydroxyl, amino, alkylideneamino having up    to 4 carbon atoms, represents in each case optionally halogen- or    C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or    alkanoylamino having in each case up to 6 carbon atoms in the alkyl    groups, represents in each case optionally halogen-substituted    alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon    atoms in the alkenyl or alkinyl groups, represents in each case    optionally halogen-substituted cycloalkyl, cycloalkylalkyl or    cycloalkylamino having in each case 3 to 6 carbon atoms in the    cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl    moiety, or represents in each case optionally halogen-, C₁-C₄-alkyl-    or C₁-C₄-alkoxy-substituted phenyl or benzyl, or together with an    adjacent radical R⁵ or R⁶ represents optionally halogen- or    C₁-C₄-alkyl-substituted alkanediyl having 3 to 5 carbon atoms,    where the individual radicals R⁵ and R⁶—if two or more of them are    attached to the same heterocyclic groupings, may have identical or    different meanings in the context of the above definition.-   A particularly preferably represents a single bond, methylene,    ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl).-   R¹ particularly preferably represents hydrogen, represents in each    case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,    methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,    methylsulphonyl-, ethylsulphonyl-, n- or    i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-    or s-butyl, or represents methoxycarbonyl, ethoxycarbonyl, n- or    i-propoxycarbonyl.-   R² particularly preferably represents methyl, ethyl, n- or i-propyl,    or together with R¹ represents methylene, ethane-1,1-diyl    (ethylidene, —CH(CH₃)—), ethane-1,2-diyl (dimethylene, —CH₂CH₂—),    propane-1,3-diyl (trimethylene, —CH₂CH₂CH₂—), butane-1,4-diyl    (tetramethylene, —CH₂CH₂CH₂CH₂)—) or pentane-1,5-diyl    (pentamethylene, —CH₂CH₂CH₂CH₂CH₂—), where in this case m represents    1 and R¹ and R² are located at the same carbon atom (“geminal”) or    at two adjacent carbon atoms (“vicinal”).-   R³ particularly preferably represents hydrogen, nitro, cyano,    carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,    iodine, represents in each case optionally fluorine- and/or    chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,    ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-,    methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or    i-propyl, n-, i-, s- or t-butyl, represents in each case optionally    fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents    in each case optionally fluorine-and/or; chlorine-substituted    methylthio, ethylthio, n- or i-propylthio, methyl-sulphinyl,    ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,    ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino,    ethyl-amino, n- or i-propylamino, dimethylamino, diethylamino,    dimethylamino-sulphonyl or diethylaminosulphonyl.-   R⁴ particularly preferably represents nitro, cyano, carboxyl,    carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents in    each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-,    n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,    methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-or    ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-    or t-butyl, represents in each case optionally fluorine- and/or    chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy,    ethoxy, n- or i-propoxy, represents in each case optionally    fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or    i-propylthio, methylsulphinyl, ethylsulphinyl, n- or    i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or    i-propylsulphonyl, or represents methylamino, ethylamino, n- or    i-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl    or diethylaminosulphonyl.-   Z particularly preferably represents the heterocyclic grouping below

R⁵ particularly preferably represents hydrogen, hydroxyl, mercapto,cyano, fluorine, chlorine, bromine, iodine, represents in each caseoptionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-,n-, i-, s- or t-butylthio-, methylsulphinyl-, ethylsulphinyl-, n- ori-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- ori-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, representsmethylamino, ethylamino, n- or i-propylamino, n-, i-, s- ort-butylamino, dimethylamino, diethylamino, di-n-propylamino ordi-1-propylamino, represents in each case optionally fluorine- and/orchlorine-substituted ethenyl, propenyl, butenenyl, ethinyl, propinyl,butinyl, propenyloxy, butenyloxy, propenylthio, butenylthio,propenylamino or butenylamino, represents in each case optionallyfluorine-and/or chlorine-substituted cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,cyclohexyloxy, cyclo-propylthio, cyclobutylthio, cyclopentylthio,cyclohexylthio, cyclopropyl-amino, cyclobutylamino, cyclopentylamino,cyclohexylamino, cyclopropyl-methyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, or represents in eachcase optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-,n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substitutedphenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy,benzylthio or benzylamino, or—in the case that two adjacent radicals R⁵and R⁵ are located at a double bond—together with the adjacent radicalR⁵ also represents a benzo grouping,

-   R⁶ particularly preferably represents hydrogen, hydroxyl, amino,    represents in each case optionally fluorine- and/or chlorine-,    methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-    or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino,    ethylamino or dimethylamino, represents in each case optionally    fluorine- and/or chlorine-substituted ethenyl, propenyl, ethinyl,    propinyl or propenyloxy, represents in each case optionally    fluorine-and/or chlorine-substituted cyclopropyl, cyclobutyl,    cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,    cyclopentylmethyl or cyclohexyl-methyl, or represents in each case    optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-,    n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or    i-propoxy-substituted phenyl or benzyl, or together with an adjacent    radical R⁵ or R⁶ represents in each case optionally methyl- and/or    ethyl-substituted propane-1,3-diyl (trimethylene), butane-1,4-diyl    (tetramethylene) or pentane-1,5-diyl (pentamethylene),    where the individual radicals R⁵ and R⁶—if two or more of them are    attached to the same heterocyclic groupings, may have identical or    different meanings in the context of the above definition.-   A very particularly preferably represents a single bond or    represents methylene.-   R¹ very particularly preferably represents hydrogen, methyl, ethyl,    n- or i-propyl.-   R² very particularly preferably represents methyl.-   R³ very particularly preferably represents hydrogen, nitro, cyano,    fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl,    methoxymethyl, methylthiomethyl, methylsulphinylmethyl,    methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,    trifluoromethoxy, methylthio, ethylthio, methyl-sulphinyl,    ethylsulphinyl, methylsulphonyl, ethylsulphonyl or    dimethyl-aminosulphonyl.-   R⁴ very particularly preferably represents nitro, cyano, fluorine,    chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxymethyl,    methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl,    methoxy, ethoxy, difluoro-methoxy, trifluoromethoxy, methylthio,    ethylthio, methylsulphinyl, ethyl-sulphinyl, methylsulphonyl,    ethylsulphonyl or dimethylaminosulphonyl.-   R⁵ very particularly preferably represents hydrogen, hydroxyl,    chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or    t-butyl, difluoromethyl, dichloro-methyl, trifluoromethyl,    trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl,    fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl,    fluoro-n-propyl, fluoro-1-propyl, chloro-n-propyl, chloro-1-propyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, fluoroethoxy,    chloroethoxy, difluoroethoxy, dichloro-ethoxy, trifluoroethoxy,    trichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy,    fluorodichloroethoxy, methylthio, ethylthio, n- or i-propylthio,    fluoroethylthio, chloroethylthio, difluoroethylthio,    dichloroethylthio, chloro-fluoroethylthio, chlorodifluoroethylthio,    fluorodichloroethylthio, methylsulphinyl, ethylsulphinyl, n- or    i-propylsulphinyl, methylsulphonyl, ethyl-sulphonyl, n- or    i-propylsulphonyl, dimethylamino, propenylthio, butenylthio,    propinylthio, butinylthio, cyclopropyl, cyclopropylmethyl,    cyclopropylmethoxy, phenyl or phenoxy.-   R⁶ very particularly preferably represents amino, methyl, ethyl, n-    or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylamino,    dimethylamino, cycloproypyl or cyclopropylmethyl, or together with    R⁵ represents propane-1,3-diyl (trimethylene), butane-1,4-diyl    (tetramethylene) or pentane-1,5-diyl (penta-methylene).-   A most preferably represents methylene.

The invention preferably provides the sodium, potassium, magnesium,calcium, ammonium, C₁-C₄-alkyl-ammonium-, di-(C₁-C₄-alkyl)-ammonium-,tri-(C₁-C₄-alkyl)-ammonium-, tetra-(C₁-C₄-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-sulphonium. C₅₋ or C₆-cycloalkyl-ammonium anddi-(C₁-C₂-alkyl)-benzyl-ammonium salts of the compounds of the formula(I), in which m, n, A, R¹, R², R³, R⁴ and Z are each as defined above.

Preference according to the invention is given to compounds of theformula (I) which contain a combination of the meanings mentioned aboveas being preferred.

Particular preference according to the invention is given to compoundsof the formula (I) which contain a combination of the meanings listedabove as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Compounds of the general formulae (IA), (IB) and (IC) below areparticularly emphasized as being according to the invention:

in which

-   m represents the numbers 0, 1 or 2,-   n represents the numbers 0, 1 or 2,-   A particularly preferably represents a single bond or represents    methylene,-   Q represents oxygen or sulphur,-   R¹ represents hydrogen, methyl, ethyl, n- or i-propyl,-   R² represents methyl,-   R³ represents hydrogen, nitro, cyano, fluorine, chlorine, bromine,    iodine, methyl. ethyl, trifluoromethyl, methoxymethyl,    methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl,    methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio,    ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,    ethylsulphonyl or dimethylaminosulphonyl.-   R⁴ represents nitro, cyano, fluorine, chlorine, bromine, methyl,    ethyl, trifluoromethyl, methoxymethyl, methylthiomethyl,    methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy,    difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,    methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or    dimethylaminosulphonyl,-   R⁵ represents hydrogen, hydroxyl, chlorine, bromine, methyl, ethyl,    n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl,    dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl,    chloroethyl, difluoroethyl, dichloroethyl, fluoro-n-propyl,    fluoro-1-propyl, chloro-n-propyl, chloro-1-propyl, methoxymethyl,    ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- or    i-propoxy, n-, i-, s- or t-butoxy, fluoroethoxy, chloroethoxy,    difluoroethoxy, dichloroethoxy, trifluoroethoxy, trichloroethoxy,    chlorofluoroethoxy, chlorodifluoroethoxy, fluorodichloroethoxy,    methylthio, ethylthio, n- or i-propylthio, fluoroethylthio,    chloroethylthio, difluoroethylthio, dichloroethylthio,    chlorofluoroethylthio, chlorodifluoroethylthio,    fluorodichloroethylthio, methylsulphinyl, ethylsulphinyl, n- or    i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or    i-propylsulphonyl, dimethylamino, propenylthio, butenylthio,    propinylthio, butinylthio, cyclopropyl, cyclopropylmethyl,    cyclopropylmethoxy, phenyl or phenoxy, and-   R⁶ represents amino, methyl, ethyl, n- or i-propyl, n-, i-, s- or    t-butyl, methoxy, ethoxy, methylamino, dimethylamino, cyclopropyl or    cyclopropylmethyl, or together with R⁵ represents propane-1,3-diyl    (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl    (pentamethylene).

Here, very particular emphasis is given to the compounds of the formula(IA) in which A represents methylene.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and also, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotherat will, i.e. including combinations between the given preferred ranges.

Examples of compounds of the general formula (I) according to theinvention are listed in the groups below.

Here, R³, (R⁴)_(n), R⁵ and R⁶ each have, for example, the meanings givenin the table below:

R³ (position-) (R⁴)_(n) R⁵ R⁶ H — CF₃ CH₃ F — CF₃ CH₃ Cl — CF₃ CH₃ Br —CF₃ CH₃ I — CF₃ CH₃ NO₂ — CF₃ CH₃ CN — CF₃ CH₃ CH₃ — CF₃ CH₃ OCH₃ — CF₃CH₃ CF₃ — CF₃ CH₃ OCHF₂ — CF₃ CH₃ OCF₃ — CF₃ CH₃ SO₂CH₃ — CF₃ CH₃ H —OCH₃ CH₃ F — OCH₃ CH₃ Cl — OCH₃ CH₃ Br — OCH₃ CH₃ I — OCH₃ CH₃ NO₂ —OCH₃ CH₃ CN — OCH₃ CH₃ CH₃ — OCH₃ CH₃ OCH₃ — OCH₃ CH₃ CF₃ — OCH₃ CH₃OCHF₂ — OCH₃ CH₃ OCF₃ — OCH₃ CH₃ SO₂CH₃ — OCH₃ CH₃ H — SCH₃ CH₃ F — SCH₃CH₃ Cl — SCH₃ CH₃ Br — SCH₃ CH₃ I — SCH₃ CH₃ NO₂ — SCH₃ CH₃ CN — SCH₃CH₃ CH₃ — SCH₃ CH₃ OCH₃ — SCH₃ CH₃ CF₃ — SCH₃ CH₃ OCHF₂ — SCH₃ CH₃ OCF₃— SCH₃ CH₃ SO₂CH₃ — SCH₃ CH₃ H — OC₂H₅ CH₃ F — OC₂H₅ CH₃ Cl — OC₂H₅ CH₃Br — OC₂H₅ CH₃ I — OC₂H₅ CH₃ NO₂ — OC₂H₅ CH₃ CN — OC₂H₅ CH₃ CH₃ — OC₂H₅CH₃ OCH₃ — OC₂H₅ CH₃ CF₃ — OC₂H₅ CH₃ OCHF₂ — OC₂H₅ CH₃ OCF₃ — OC₂H₅ CH₃SO₂CH₃ — OC₂H₅ CH₃ H — N(CH₃)₂ CH₃ F — N(CH₃)₂ CH₃ Cl — N(CH₃)₂ CH₃ Br —N(CH₃)₂ CH₃ I — N(CH₃)₂ CH₃ NO₂ — N(CH₃)₂ CH₃ CN — N(CH₃)₂ CH₃ CH₃ —N(CH₃)₂ CH₃ OCH₃ — N(CH₃)₂ CH₃ CF₃ — N(CH₃)₂ CH₃ OCHF₂ — N(CH₃)₂ CH₃OCF₃ — N(CH₃)₂ CH₃ SO₂CH₃ — N(CH₃)₂ CH₃ H — OCH₃

F — OCH₃

Cl — OCH₃

Br — OCH₃

I — OCH₃

NO₂ — OCH₃

CN — OCH₃

CH₃ — OCH₃

OCH₃ — OCH₃

CF₃ — OCH₃

OCHF₂ — OCH₃

OCF₃ — OCH₃

SO₂CH₃ — OCH₃

H (3-) Cl CF₃ CH₃ F (3-) Cl CH₃ CH₃ Cl (3-) Cl OCH₃ CH₃ Br (3-) Cl Br

Cl (3-) Cl CF₃ CH₃ NO₂ (3-) Cl CH₃ CH₃ Cl (3-) Cl SCH₃ CH₃ CH₃ (3-) ClCl CH₃ OCH₃ (3-) Cl OCH₃ CH₃ CF₃ (3-) Cl CF₃ CH₃ OCHF₂ (3-) Cl CH₃ CH₃OCF₃ (3-) Cl CH₃ CH₃ SO₂CH₃ (3-) Cl OCH₃ CH₃

Here R³, (R⁴)_(n), R⁵ and R⁶ each have, for example, the meanings givenin the table below:

R³ (position-) (R⁴)_(n) R⁵ R⁶ Cl (2-) Cl CF₃ CH₃ Cl (2-) Cl SCH₃ CH₃ Cl(2-) Cl SC₂H₅ CH₃ Cl (2-) Cl SC₃H₇ CH₃ Cl (2-) Cl SC₃H₇-i CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl SCH═C═CH₂ CH₃ Cl (2-) Cl SCH₂CN CH₃ Cl (2-) Cl SCH₂CH₂CNCH₃ Cl (2-) Cl OCH₃ CH₃ Cl (2-) Cl OC₂H₅ CH₃ Cl (2-) Cl OC₃H₇ CH₃ Cl(2-) Cl OC₃H₇-i CH₃ Cl (2-) Cl OC₄H₉ CH₃ Cl (2-) Cl OCH₂CF₃ CH₃ Cl (2-)Cl

CH₃ Cl (2-) Cl OC₆H₅ CH₃ Cl (2-) Cl H CH₃ Cl (2-) Cl CH₃ CH₃ Cl (2-) ClC₂H₅ CH₃ Cl (2-) Cl C₃H₇ CH₃ Cl (2-) Cl C₃H₇-i CH₃ Cl (2-) Cl C₄H₉ CH₃Cl (2-) Cl C₄H₉-i CH₃ Cl (2-) Cl C₄H₉-s CH₃ Cl (2-) Cl C₄H₉-t CH₃ Cl(2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl CH═CHCH₃ CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl N(CH₃)₂ CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl Cl CH₃ Cl (2-) Cl Br CH₃ SO₂CH₃ (2-) Cl CF₃ CH₃ SO₂CH₃(2-) Cl SCH₃ CH₃ SO₂CH₃ (2-) Cl SC₂H₅ CH₃ SO₂CH₃ (2-) Cl SC₃H₇ CH₃SO₂CH₃ (2-) Cl SC₃H₇-i CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl SCH═C═CH₂ CH₃ SO₂CH₃ (2-) Cl SCH₂CN CH₃ SO₂CH₃ (2-)Cl SCH₂CH₂CN CH₃ SO₂CH₃ (2-) Cl OCH₃ CH₃ SO₂CH₃ (2-) Cl OC₂H₅ CH₃ SO₂CH₃(2-) Cl OC₃H₇ CH₃ SO₂CH₃ (2-) Cl OC₃H₇-i CH₃ SO₂CH₃ (2-) Cl OC₄H₉ CH₃SO₂CH₃ (2-) Cl OCH₂CF₃ CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl OC₆H₅ CH₃ SO₂CH₃ (2-) Cl H CH₃ SO₂CH₃ (2-) Cl CH₃ CH₃SO₂CH₃ (2-) Cl C₂H₅ CH₃ SO₂CH₃ (2-) Cl C₃H₇ CH₃ SO₂CH₃ (2-) Cl C₃H₇-iCH₃ SO₂CH₃ (2-) Cl C₄H₉ CH₃ SO₂CH₃ (2-) Cl C₄H₉-i CH₃ SO₂CH₃ (2-) ClC₄H₉-s CH₃ SO₂CH₃ (2-) Cl C₄H₉-t CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl CH═CHCH₃ CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl N(CH₃)₂ CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl Cl CH₃ SO₂CH₃ (2-) Cl Br CH₃ Cl (2-) SO₂CH₃ CF₃ CH₃Cl (2-) SO₂CH₃ SCH₃ CH₃ Cl (2-) SO₂CH₃ SC₂H₅ CH₃ Cl (2-) SO₂CH₃ SC₃H₇CH₃ Cl (2-) SO₂CH₃ SC₃H₇-i CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ SCH═C═CH₂ CH₃ Cl (2-) SO₂CH₃ SCH₂CN CH₃ Cl (2-)SO₂CH₃ SCH₂CH₂CN CH₃ Cl (2-) SO₂CH₃ OCH₃ CH₃ Cl (2-) SO₂CH₃ OC₂H₅ CH₃ Cl(2-) SO₂CH₃ OC₃H₇ CH₃ Cl (2-) SO₂CH₃ OC₃H₇-i CH₃ Cl (2-) SO₂CH₃ OC₄H₉CH₃ Cl (2-) SO₂CH₃ OCH₂CF₃ CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ OC₆H₅ CH₃ Cl (2-) SO₂CH₃ H CH₃ Cl (2-) SO₂CH₃ CH₃ CH₃Cl (2-) SO₂CH₃ C₂H₅ CH₃ Cl (2-) SO₂CH₃ C₃H₇ CH₃ Cl (2-) SO₂CH₃ C₃H₇-iCH₃ Cl (2-) SO₂CH₃ C₄H₉ CH₃ Cl (2-) SO₂CH₃ C₄H₉-i CH₃ Cl (2-) SO₂CH₃C₄H₉-s CH₃ Cl (2-) SO₂CH₃ C₄H₉-t CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ CH═CHCH₃ CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ N(CH₃)₂ CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ Cl CH₃ Cl (2-) SO₂CH₃ Br CH₃ Cl (2-) Cl CF₃

Cl (2-) Cl SCH₃

Cl (2-) Cl SC₂H₅

Cl (2-) Cl SC₃H₇

Cl (2-) Cl SC₃H₇-i

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl SCH═C═CH₂

Cl (2-) Cl SCH₂CN

Cl (2-) Cl SCH₂CH₂CN

Cl (2-) Cl OCH₃

Cl (2-) Cl OC₂H₅

Cl (2-) Cl OC₃H₇

Cl (2-) Cl OC₃H₇-i

Cl (2-) Cl OC₄H₉

Cl (2-) Cl OCH₂CF₃

Cl (2-) Cl

Cl (2-) Cl OC₆H₅

Cl (2-) Cl H

Cl (2-) Cl CH₃

Cl (2-) Cl C₂H₅

Cl (2-) Cl C₃H₇

Cl (2-) Cl C₃H₇-i

Cl (2-) Cl C₄H₉

Cl (2-) Cl C₄H₉-i

Cl (2-) Cl C₄H₉-s

Cl (2-) Cl C₄H₉-t

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl CH═CHCH₃

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl N(CH₃)₂

Cl (2-) Cl

Cl (2-) Cl Cl

Cl (2-) Cl Br

SO₂CH₃ (2-) Cl CF₃

SO₂CH₃ (2-) Cl SCH₃

SO₂CH₃ (2-) Cl SC₂H₅

SO₂CH₃ (2-) Cl SC₃H₇

SO₂CH₃ (2-) Cl SC₃H₇-i

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl SCH═C═CH₂

SO₂CH₃ (2-) Cl SCH₂CN

SO₂CH₃ (2-) Cl SCH₂CH₂CN

SO₂CH₃ (2-) Cl OCH₃

SO₂CH₃ (2-) Cl OC₂H₅

SO₂CH₃ (2-) Cl OC₃H₇

SO₂CH₃ (2-) Cl OC₃H₇-i

SO₂CH₃ (2-) Cl OC₄H₉

SO₂CH₃ (2-) Cl OCH₂CF₃

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl OC₆H₅

SO₂CH₃ (2-) Cl H

SO₂CH₃ (2-) Cl CH₃

SO₂CH₃ (2-) Cl C₂H₅

SO₂CH₃ (2-) Cl C₃H₇

SO₂CH₃ (2-) Cl C₃H₇-i

SO₂CH₃ (2-) Cl C₄H₉

SO₂CH₃ (2-) Cl C₄H₉-i

SO₂CH₃ (2-) Cl C₄H₉-s

SO₂CH₃ (2-) Cl C₄H₉-t

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl CH═CHCH₃

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl N(CH₃)₂

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl Cl

SO₂CH₃ (2-) Cl Br

Cl (2-) SO₂CH₃ CF₃

Cl (2-) SO₂CH₃ SCH₃

Cl (2-) SO₂CH₃ SC₂H₅

Cl (2-) SO₂CH₃ SC₃H₇

Cl (2-) SO₂CH₃ SC₃H₇-i

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ SCH═C═CH₂

Cl (2-) SO₂CH₃ SCH₂CN

Cl (2-) SO₂CH₃ SCH₂CH₂CN

Cl (2-) SO₂CH₃ OCH₃

Cl (2-) SO₂CH₃ OC₂H₅

Cl (2-) SO₂CH₃ OC₃H₇

Cl (2-) SO₂CH₃ OC₃H₇-i

Cl (2-) SO₂CH₃ OC₄H₉

Cl (2-) SO₂CH₃ OCH₂CF₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ OC₆H₅

Cl (2-) SO₂CH₃ H

Cl (2-) SO₂CH₃ CH₃

Cl (2-) SO₂CH₃ C₂H₅

Cl (2-) SO₂CH₃ C₃H₇

Cl (2-) SO₂CH₃ C₃H₇-i

Cl (2-) SO₂CH₃ C₄H₉

Cl (2-) SO₂CH₃ C₄H₉-i

Cl (2-) SO₂CH₃ C₄H₉-s

Cl (2-) SO₂CH₃ C₄H₉-t

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ CH═CHCH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO_(2CH) ₃ N(CH₃)₂

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ Cl

Cl (2-) SO₂CH₃ Br

Cl (2-) Cl CF₃ N(CH₃)₂ Cl (2-) Cl SCH₃ N(CH₃)₂ Cl (2-) Cl SC₂H₅ N(CH₃)₂Cl (2-) Cl SC₃H₇ N(CH₃)₂ Cl (2-) Cl SC₃H₇-i N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl SCH═C═CH₂ N(CH₃)₂ Cl (2-) Cl SCH₂CN N(CH₃)₂ Cl (2-)Cl SCH₂CH₂CN N(CH₃)₂ Cl (2-) Cl OCH₃ N(CH₃)₂ Cl (2-) Cl OC₂H₅ N(CH₃)₂ Cl(2-) Cl OC₃H₇ N(CH₃)₂ Cl (2-) Cl OC₃H₇-i N(CH₃)₂ Cl (2-) Cl OC₄H₉N(CH₃)₂ Cl (2-) Cl OCH₂CF₃ N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl OC₆H₅ N(CH₃)₂ Cl (2-) Cl H N(CH₃)₂ Cl (2-) Cl CH₃N(CH₃)₂ Cl (2-) Cl C₂H₅ N(CH₃)₂ Cl (2-) Cl C₃H₇ N(CH₃)₂ Cl (2-) ClC₃H₇-i N(CH₃)₂ Cl (2-) Cl C₄H₉ N(CH₃)₂ Cl (2-) Cl C₄H₉-i N(CH₃)₂ Cl (2-)Cl C₄H₉-s N(CH₃)₂ Cl (2-) Cl C₄H₉-t N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl CH═CHCH₃ N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl Cl N(CH₃)₂ Cl (2-) Cl Br N(CH₃)₂ SO₂CH₃ (2-) Cl CF₃N(CH₃)₂ SO₂CH₃ (2-) Cl SCH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl SC₂H₅ N(CH₃)₂ SO₂CH₃(2-) Cl SC₃H₇ N(CH₃)₂ SO₂CH₃ (2-) Cl SC₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl SCH═C═CH₂ N(CH₃)₂ SO₂CH₃ (2-) Cl SCH₂CN N(CH₃)₂SO₂CH₃ (2-) Cl SCH₂CH₂CN N(CH₃)₂ SO₂CH₃ (2-) Cl OCH₃ N(CH₃)₂ SO₂CH₃ (2-)Cl OC₂H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl OC₃H₇ N(CH₃)₂ SO₂CH₃ (2-) Cl OC₃H₇-iN(CH₃)₂ SO₂CH₃ (2-) Cl OC₄H₉ N(CH₃)₂ SO₂CH₃ (2-) Cl OCH₂CF₃ N(CH₃)₂SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl OC₆H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl H N(CH₃)₂ SO₂CH₃(2-) Cl CH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl C₂H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl C₃H₇N(CH₃)₂ SO₂CH₃ (2-) Cl C₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) Cl C₄H₉ N(CH₃)₂ SO₂CH₃(2-) Cl C₄H₉-i N(CH₃)₂ SO₂CH₃ (2-) Cl C₄H₉-s N(CH₃)₂ SO₂CH₃ (2-) ClC₄H₉-t N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl CH═CHCH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl Cl N(CH₃)₂ SO₂CH₃ (2-) Cl Br N(CH₃)₂ Cl (2-)SO₂CH₃ CF₃ N(CH₃)₂ Cl (2-) SO₂CH₃ SCH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ SC₂H₅N(CH₃)₂ Cl (2-) SO₂CH₃ SC₃H₇ N(CH₃)₂ Cl (2-) SO₂CH₃ SC₃H₇-i N(CH₃)₂ Cl(2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ SCH═C═CH₂ N(CH₃)₂ Cl (2-) SO₂CH₃ SCH₂CN N(CH₃)₂Cl (2-) SO₂CH₃ SCH₂CH₂CN N(CH₃)₂ Cl (2-) SO₂CH₃ OCH₃ N(CH₃)₂ Cl (2-)SO₂CH₃ OC₂H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ OC₃H₇ N(CH₃)₂ Cl (2-) SO₂CH₃ OC₃H₇-iN(CH₃)₂ Cl (2-) SO₂CH₃ OCH₄H₉ N(CH₃)₂ Cl (2-) SO₂CH₃ OCH₂CF₃ N(CH₃)₂ Cl(2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ OC₆H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ H N(CH₃)₂ Cl (2-)SO₂CH₃ CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ C₂H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ C₃H₇N(CH₃)₂ Cl (2-) SO₂CH₃ C₃H₇-i N(CH₃)₂ Cl (2-) SO₂CH₃ C₄H₉ N(CH₃)₂ Cl(2-) SO₂CH₃ C₄H₉-i N(CH₃)₂ Cl (2-) SO₂CH₃ C₄H₉-s N(CH₃)₂ Cl (2-) SO₂CH₃C₄H₉-t N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ CH═CHCH₃ N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ Cl N(CH₃)₂ Cl (2-) SO₂CH₃ Br N(CH₃)₂ Cl (2-) ClCH₃ OCH₃ Cl (2-) Cl C₂H₅ OCH₃ Cl (2-) Cl C₃H₇ OCH₃ Cl (2-) Cl SCH₃ OCH₃Cl (2-) Cl SC₂H₅ OCH₃ Cl (2-) Cl OCH₃ OCH₃ Cl (2-) Cl OC₂H₅ OCH₃ Cl (2-)Cl CH₃ OC₂H₅ Cl (2-) Cl C₂H₅ OC₂H₅ Cl (2-) Cl C₃H₇ OC₂H₅ Cl (2-) Cl SCH₃OC₂H₅ Cl (2-) Cl SC₂H₅ OC₂H₅ Cl (2-) Cl OCH₃ OC₂H₅ Cl (2-) Cl OC₂H₅OC₂H₅ Cl (2-) SO₂CH₃ CH₃ OCH₃ Cl (2-) SO₂CH₃ C₂H₅ OCH₃ Cl (2-) SO₂CH₃C₃H₇ OCH₃ Cl (2-) SO₂CH₃ SCH₃ OCH₃ Cl (2-) SO₂CH₃ SC₂H₅ OCH₃ Cl (2-)SO₂CH₃ OCH₃ OCH₃ Cl (2-) SO₂CH₃ OC₂H₅ OCH₃ Cl (2-) SO₂CH₃ CH₃ OC₂H₅ Cl(2-) SO₂CH₃ C₂H₅ OC₂H₅ Cl (2-) SO₂CH₃ C₃H₇ OC₂H₅ Cl (2-) SO₂CH₃ SCH₃OC₂H₅ Cl (2-) SO₂CH₃ SC₂H₅ OC₂H₅ Cl (2-) SO₂CH₃ OCH₃ OC₂H₅ Cl (2-)SO₂CH₃ OC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl Cl OCH₃ SO₂CH₃ (2-) Cl Br OCH₃ SO₂CH₃(2-) Cl CH₃ OCH₃ SO₂CH₃ (2-) Cl C₂H₅ OCH₃ SO₂CH₃ (2-) Cl C₃H₇ OCH₃SO₂CH₃ (2-) Cl SCH₃ OCH₃ SO₂CH₃ (2-) Cl SC₂H₅ OCH₃ SO₂CH₃ (2-) Cl OCH₃OC₂H₅ SO₂CH₃ (2-) Cl OC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl CH₃ OC₂H₅ SO₂CH₃ (2-) ClC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl C₃H₇ OC₂H₅ SO₂CH₃ (2-) Cl SCH₃ OC₂H₅ SO₂CH₃(2-) Cl SC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl OCH₃ OC₂H₅ CF₃ (2-) Cl Br CH₃ CF₃(2-) Cl SCH₃ CH₃ CF₃ (2-) Cl OCH₃ CH₃ CF₃ (2-) Cl N(CH₃)₂ CH₃ CF₃ (2-)Cl CF₃ CH₃ CF₃ (2-) NO₂ Br CH₃ CF₃ (2-) NO₂ SCH₃ CH₃ CF₃ (2-) NO₂ OCH₃CH₃ CF₃ (2-) NO₂ N(CH₃)₂ CH₃ CF₃ (2-) NO₂ CF₃ CH₃ CF₃ (2-) CH₃ Br CH₃CF₃ (2-) CH₃ SCH₃ CH₃ CF₃ (2-) CH₃ OCH₃ CH₃ CF₃ (2-) CH₃ N(CH₃)₂ CH₃ CF₃(2-) CH₃ CF₃ CH₃ CF₃ (2-) OCH₃ Br CH₃ CF₃ (2-) OCH₃ SCH₃ CH₃ CF₃ (2-)OCH₃ OCH₃ CH₃ CF₃ (2-) OCH₃ N(CH₃)₂ CH₃ CF₃ (2-) OCH₃ CF₃ CH₃ SO₂CH₃(2-) NO₂ Br CH₃ SO₂CH₃ (2-) NO₂ SCH₃ CH₃ SO₂CH₃ (2-) NO₂ OCH₃ CH₃ SO₂CH₃(2-) NO₂ N(CH₃)₂ CH₃ SO₂CH₃ (2-) NO₂ CF₃ CH₃ SO₂CH₃ (2-) CF₃ Br CH₃SO₂CH₃ (2-) CF₃ SCH₃ CH₃ SO₂CH₃ (2-) CF₃ OCH₃ CH₃ SO₂CH₃ (2-) CF₃N(CH₃)₂ CH₃ SO₂CH₃ (2-) CF₃ CF₃ CH₃ SO₂CH₃ (2-) SO₂CH₃ Br CH₃ SO₂CH₃(2-) SO₂CH₃ SCH₃ CH₃ SO₂CH₃ (2-) SO₂CH₃ OCH₃ CH₃ SO₂CH₃ (2-) SO₂CH₃N(CH₃)₂ CH₃ SO₂CH₃ (2-) SO₂CH₃ CF₃ CH₃ CN (2-) Cl Br CH₃ CN (2-) Cl SCH₃CH₃ CN (2-) Cl OCH₃ CH₃ CN (2-) Cl N(CH₃)₂ CH₃ CN (2-) Cl CF₃ CH₃ CN(2-) NO₂ Br CH₃ CN (2-) NO₂ SCH₃ CH₃ CN (2-) NO₂ OCH₃ CH₃ CN (2-) NO₂N(CH₃)₂ CH₃ CN (2-) NO₂ CF₃ CH₃ CN (2-) CF₃ Br CH₃ CN (2-) CF₃ SCH₃ CH₃CN (2-) CF₃ OCH₃ CH₃ CN (2-) CF₃ N(CH₃)₂ CH₃ CN (2-) CF₃ CF₃ CH₃ CN (2-)SO₂CH₃ Br CH₃ CN (2-) SO₂CH₃ SCH₃ CH₃ CN (2-) SO₂CH₃ OCH₃ CH₃ CN (2-)SO₂CH₃ N(CH₃)₂ CH₃ CN (2-) SO₂CH₃ CF₃ CH₃ Br (2-) NO₂ Br CH₃ Br (2-) NO₂SCH₃ CH₃ Br (2-) NO₂ OCH₃ CH₃ Br (2-) NO₂ N(CH₃)₂ CH₃ Br (2-) NO₂ CF₃CH₃ Br (2-) CF₃ Br CH₃ Br (2-) CF₃ SCH₃ CH₃ Br (2-) CF₃ OCH₃ CH₃ Br (2-)CF₃ N(CH₃)₂ CH₃ Br (2-) CF₃ CF₃ CH₃ Br (2-) SO₂CH₃ Br CH₃ Br (2-) SO₂CH₃SCH₃ CH₃ Br (2-) SO₂CH₃ OCH₃ CH₃ Br (2-) SO₂CH₃ N(CH₃)₂ CH₃ Br (2-)SO₂CH₃ CF₃ CH₃ Br (2-) CH₃ Br CH₃ Br (2-) CH₃ SCH₃ CH₃ Br (2-) CH₃ OCH₃CH₃ Br (2-) CH₃ N(CH₃)₂ CH₃ Br (2-) CH₃ CF₃ CH₃

Here, R³, (R⁴)_(n), R⁵ and R⁶ each have, for example, the meanings givenabove in Group 1.

Here, R³, (R⁴)_(n), R⁵ and R⁶ each have, for example, the meanings givenabove in Group 2.

The novel substituted benzoylcyclohexanediones of the general formula(I) have strong and selective herbicidal activity.

The novel substituted benzoylcyclohexanediones of the general formula(I) are obtained when 1,3-cyclohexanedione or its derivatives of thegeneral formula (II),

in which

-   m R¹ and R² are each as defined above.-   are reacted with substituted benzoic acids of the general formula    (III).    in which-   n, A, R³, R⁴ and Z are each as defined above,    in the presence of a dehydrating agent, if appropriate in the    presence of one or more reaction auxiliaries and if appropriate in    the presence of a diluent,    and, if appropriate, the compounds of the formula (I) obtained in    this manner are subsequently subjected in a customary manner, within    the scope of the definition of the substituents, to electrophilic or    nucleophilic or oxidation or reduction reactions, or the compounds    of the formula (I) are converted in a customary manner into salts.

The compounds of the formula (I) can be converted into other compoundsof the formula (I) in accordance with the definition above usingcustomary methods, for example by nucleophilic substitution (for exampleR⁵: Cl→OC₂H₅, SCH₃) or by oxidation (for example R⁵:CH₂SCH₃→CH₂S(O)CH₃).

In principle, the compounds of the general formula (I) can also besynthesized as shown schematically below:

Reaction of 1,3-cyclohexanedione or its derivatives of the generalformula (II)—above—with reactive derivatives of the substituted benzoicacids of the general formula (III)—above—in particular with thecorresponding carbonyl chlorides, carboxylic anhydrides, carboxylic acidcyanides, methyl carboxylates or ethyl carboxylates—if appropriate inthe presence of reaction auxiliaries, such as, for example,triethylamine (and, if appropriate, additionally zinc chloride), and, ifappropriate, in the presence of a diluent, such as, for example,methylene chloride:

In the reactions outlined above for preparing the compounds of thegeneral formula (I), there is, in addition to the desired C-benzoylationat the cyclohexanedione, also an O-benzoylation—cf. equation below (cf.Synthesis 1978, 925-927; Tetrahedron Lett. 37 (1996), 1007-1009,WO-A-91/05469). However, the O-benzoyl compounds formed in this processare, under the reaction conditions of the process according to theinvention, isomerized to the corresponding C-benzoyl compounds of theformula (I).

Using, for example, 1,3-cyclohexanedione and2-(3-carboxy-5-fluorobenzyl)-5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of the reaction in the processaccording to the invention can be outlined by the following equation:

The formula (II) provides a general definition of the cyclohexanedionesto be used as starting materials in the process according to theinvention for preparing compounds of the formula (I). In the formula(II), m, R¹ and R² each preferably have those meanings which havealready been given above, in connection with the description of thecompounds of the formula (I) according to the invention, as beingpreferred, as being particularly preferred, or as being veryparticularly preferred for m, R¹ and R².

The starting materials of the general formula (II) are known and/or canbe prepared by processes known per se.

The formula (III) provides a general definition of the substitutedbenzoic acids further to be used as starting materials in the processaccording to the invention for preparing compounds of the formula (I).In the formula (III), n, A, R³, R⁴ and Z each preferably have thosemeanings which have already been given above, in connection with thedescription of the compounds of the formula (I) according to theinvention, as being preferred, as being particularly preferred, as beingvery particularly preferred or as being most preferred for n, A, R³, R⁴and Z.

Except for2-(5-carboxy-2,4-dichloro-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one-alias2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-benzoicacid (CAS-Reg.-No. 90208-77-8) and2-(5-carboxy-2,4-dichloro-phenyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one-alias2,4-dichloro-5-(4,5-dihydro-3,4-dimethyl-5-oxo-1H-1,2,4-triazol-1-yl)-benzoicacid (CAS-Reg.-No. 90208-76-7)—the starting materials of the generalformula (III) have hitherto not been disclosed in the literature. Exceptfor2-(5-carboxy-2,4-dichloro-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneand2-(5-carboxy-2,4-dichloro-phenyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one(cf. JP-A-58225070—quoted in Chem. Abstracts 100:209881,JP-A-02015069—quoted in Chem. Abstracts 113:23929), they also form, asnovel compounds, part of the subject matter of the present application.

The novel substituted benzoic acids of the general formula (III), areobtained when benzoic acid derivatives of the general formula (IV),

in which

-   n, A, R³ and R⁴ and Z are each as defined above, and-   Y represents cyano, carbamoyl, halogenocarbamoyl or alkoxycarbonyl,    are reacted with water, if appropriate in the presence of a    hydrolysis auxiliary, such as, for example, sulphuric acid, at    temperatures between 50° C. and 120° C. (cf. the Preparation    Examples).

The benzoic acid derivatives of the general formula (IV) required asprecursors are known and/or can be prepared by processes known per se(cf. DE-A-3839480 DE-A-4239296. EP-A-597360, EP-A-609734, DE-A4303676.EP-A-617026, DE-A-4405614. U.S. Pat. No. 5,378,681).

The novel substituted benzoic acids of the general formula (III) arealso obtained when halogeno(alkyl)benzoic acids of the general formula(V),

in which

-   n, A, R³ and R⁴ are each as defined above and-   X represents halogen (in particular fluorine, chlorine or bromine)    are reacted with compounds of the general formula (VI)    in which-   Z is as defined above,-   if appropriate in the presence of a reaction auxiliary, such as, for    example, triethylamine or potassium carbonate, and if appropriate in    the presence of a diluent, such as, for example, acetone,    acetonitrile, N,N-dimethyl-formamide or N,N-dimethyl-acetamide, at    temperatures between 50° C. and 200° C. (cf. the Preparation    Examples).

Instead of the halogeno(alkyl)benzoic acids of the general formula (V),it is also possible, similarly to the methods described above, to reactappropriate nitrites, amides and esters—in particular the methyl estersor the ethyl esters—with compounds of the general formula (VI). Bysubsequent hydrolysis according to customary methods, for example byreaction with aqueous-ethanolic potassium hydroxide solution, it is thenpossible to obtain the corresponding substituted benzoic acids.

The halogeno(alkyl)benzoic acids of the formula (V)—or correspondingnitriles or esters—required as precursors are known and/or can beprepared by processes known per se (cf. EP-A-90369, EP-A-93488,EP-A-399732, EP-A-480641. EP-A-609798. EP-A-763524, DE-A-2126720,WO-A-93103722. WO-A-97/38977. U.S. Pat. No. 3,978,127, U.S. Pat. No.4,837,333).

The compounds of the general formula (VI) further required as precursorsare known and/or can be prepared by processes known per se.

The process according to the invention for preparing the novelsubstituted benzoylcyclohexanediones of the general formula (I) iscarried out using a dehydrating agent. Here, suitable dehydrating agentsare the customary chemicals which are suitable for binding water.

Examples of these are dicyclohexylcarbodiimide andcarbonyl-bis-imidazole.

A particularly suitable dehydrating agent is dicyclohexylcarbodiimide.

The process according to the invention for preparing novel substitutedbenzoylcyclohexanediones of the general formula (I) is, if appropriate,carried out using a reaction auxiliary.

Examples of these are sodium cyanide, potassium cyanide, acetonecyanohydrin, 2-cyano-2-(trimethylsilyloxy)-propane and trimethylsilylcyanide.

The particularly suitable further reaction auxiliary is trimethylsilylcyanide.

The process according to the invention for preparing the novelsubstituted benzoylcyclohexanediones of the general formula (I) is, ifappropriate, carried out using a further reaction auxiliary. Suitablefurther reaction auxiliaries for the process according to the inventionare, in general, basic organic nitrogen compounds, such as, for example,trimethylamine, triethylamine, tripropylamine, tributylamine,ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine,4-dimethylamino-pyridine, N-methylpiperidine,1,4-diazabicyclo[2,2,2]-octane (DABCO),1,5-diazabicyclo[4,3,0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

Suitable diluents for carrying out the process according to theinvention are, in particular, inert organic solvents. These include, inparticular, aliphatic, alicyclic or aromatic, optionally halogenatedhydrocarbons, such as, for example, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane,dichloromethane, chloroform, tetrachloromethane or 1,2-dichloroethane;ethers, such as diethyl ether, diisopropyl ether, dioxane,tetrahydrofuran, ethylene glycol dimethyl ether or ethylene glycoldiethyl ether; ketones, such as acetone, butanone or methyl isobutylketone; nitriles, such as acetonitrile, propionitrile or butyronitrile;amides, such as N,N-dimethylformamide, N,N-dimethylacetamide,N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphorictriamide; esters such as methyl acetate or ethyl acetate, sulphoxides,such as dimethylsulphoxide.

When carrying out the process according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures between 0° C. and 150° C.,preferably between 10° C. and 120° C.

The process according to the invention is generally carried out underatmospheric pressure. However, it is also possible to carry, out theprocess according to the invention under elevated or reduced pressure—ingeneral between 0.1 bar and 10 bar.

For carrying out the process according to the invention, the startingmaterials are generally employed in approximately equimolar amounts.However, it is also possible to use a relatively large excess of one ofthe components. The reaction is generally carried out in a suitablediluent in the presence of a dehydrating agent, and the reaction mixtureis generally stirred at the required temperature for several hours.Work-up is carried out by customary methods (cf. the PreparationExamples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.By weeds in the broadest sense, there are to be understood all plantswhich grow in locations where they are not wanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal control of weeds, for example on industrial terrain and railwaytracks, and on paths and open spaces with or without tree plantings.Equally, the compounds can be employed for the control of weeds inperennial crops for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture land, and for the selective control of weeds inannual crops.

The compounds of the formula (I) according to the invention areparticularly suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous crops, both pre-emergence andpostemergence.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifying agents and/or dispersing agents and/or foam-forming agents.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Suitable liquid solvents areessentially the following: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and also water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,and also synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifying and/or foam-forming agents are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates aswell as protein hydrolysates: suitable dispersing agents are: forexample lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes, such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

The formulations in general contain between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

For the control of weeds, the active compounds according to theinvention, as such or in the form of their formulations, can also beused as mixtures with known herbicides, finished formulations or tankmixes being possible.

Possible components for the mixtures are known herbicides, for example

-   acetochlor, acifluorfen(-sodium), aclonifen, alachlor,    alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,    asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),    benfuresate, bensulfuron(-methyl), bentazon, benzofenap,    benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),    bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim,    butylate, cafenstrole, caloxydim, carbetamide,    carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon,    chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron,    cinidon(-ethyl), cinmethylin, cinosulfuron, clethodim,    clodinafop(-propargyl), clomazone, clomeprop, clopyralid,    clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron,    cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim,    cyhalofop(-butyl). 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate,    dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl),    difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate,    dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine,    diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC,    esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate,    ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl),    flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),    flazasulfuron, fluazifop(-P-butyl), fluazolate, flucarbazone,    flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin,    flumipropyn, flumetsulam, fluometuron, fluorochloridone,    fluoroglycofen(-ethyl), flupoxam, flupropacil,    flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fluridone,    fluroxypyr(-meptyl), flurprimidol, flurtamone, fluthiacet(-methyl),    fluthiamide, fomesafen, glufosinate-(-ammonium),    glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxy-ethyl),    haloxyfop(-P-methyl), hexazinone, imazamethabenz(-methyl),    imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,    imazosulfuron, iodosulfuron, ioxynil, isopropalin, isoproturon,    isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop,    lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione,    metamitron, metazachlor, methabenzthiazuron, metobenzuron,    metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin,    metsulfuron(-methyl), molinate, monolinuron, naproanilide,    napropamide, neburon, nicosulfuron, norflurazon, orbencarb,    oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone,    oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone,    phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl),    procarbazone, prometryn, propachlor, propanil, propaquizafop,    propisochlor, propyzamide, prosulfocarb, prosulfuron,    pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen,    pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl),    pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine,    quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron,    sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,    sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam,    tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor,    thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl),    thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron,    tribenuron(-methyl), triclopyr, tridiphane, trifluralin and    triflusulfuron.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing, scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES Example 1

1.2 g (3.48 mmol) of5-ethoxy-4-methyl-2-(2-carboxy-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneare suspended in 30 ml of acetonitrile and, at room temperature(approximately 20° C.), admixed with 0.39 g (3.48 mmol) of1,3-cyclohexanedione and 0.76 g (3.7 mmol) of dicyclohexylcarbodiimide(DCC). The reaction mixture is stirred at room temperature overnight(approximately 15 hours) and then admixed with 1.0 ml (7.0 mmol) oftriethylamine and 0.10 ml (1.39 mmol) of trimethylsilyl cyanide. After 3hours at room temperature, the mixture is stirred with 100 ml of 5%strength aqueous sodium carbonate solution, the dicyclohexylurea thatseparates out is filtered off with suction and the alkaline aqueousphase is repeatedly extracted with ethyl acetate. The aqueous phase isthen adjusted to pH 2 using 35% strength hydrochloric acid and extractedrepeatedly with methylene chloride. The methylene chloride phases aredried over sodium sulphate and concentrated.

This gives 0.8 g (52% of theory) of5-ethoxy-4-methyl-2-[2-(2,6-dioxo-cyclohexyl-carbonyl)-5-trifluoromethyl-benzyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneas an amorphous residue.

logP (determined at pH=2): 2.70.

Example 2

A solution of 1.5 g (7.2 mmol) of dicyclohexylcarbodiimide in 40 ml ofacetonitrile is added to a suspension of 2.15 g (6.5 mmol) of2-(4-carboxy-3-chloro-phenyl)-4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one,0.83 g (7.2 mmol) of 1,3-cyclohexanedione and 40 ml of acetonitrile, andthe reaction mixture is stirred at 20° C. for 16 hours. 1.3 g (13 mmol)of triethylamine and 0.26 g (2.6 mmol) of trimethylsilyl cyanide arethen added, and the reaction mixture is stirred at 20° C. for a further4 hours. The mixture is then stirred with 180 ml of 2% strength aqueoussodium carbonate solution and filtered off with suction. The motherliquor is extracted with ethyl acetate. The aqueous phase is thenacidified using 2N hydrochloric acid and extracted with methylenechloride. The organic phase is dried, concentrated under water pumpvacuum and digested with diethyl ether/petroleum ether. The resultingcrystalline product is isolated by filtration with suction.

This gives 1.6 g (59% of theory) of2-[4-(2,6-dioxocyclohexylcarbonyl)-3-chloro-phenyl]4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3′-oneof melting point 182° C.

logP (determined at pH=2): 3.13.

By the methods of Preparation Examples 1 and 2, and in accordance withthe general description of the preparation processes according to theinvention, it is also possible to prepare, for example, the compounds ofthe formula (I)— or of the formulae (IA-3), (IB-2), (IC-2) or(ID)—listed in Tables 1 and 2 below.

TABLE 1 Examples of compounds of the formulae (IA-3), (IB-2), (IC-2)(position) (formula) Ex. No. A R³ (R⁴)_(n) R⁵ R⁶ physical data  3 — H HCF₃ CH₃ (IC-2) logP = 2.41^(a))  4 CH₂ CF₃ H

(IA-3) logP = 2.41^(a))  5 CH₂ SO₂CH₃ H

(IB-2) m.p.: 153° C.  6 CH₂ SO₂CH₃ H CH₃ CH₃ (IA-3) m.p.: 162° C.  7 CH₂Cl H CH₃ CH₃ (IB-2) logP = 1.50^(a))  8 CH₂ Cl H CF₃ CH₃ (IB-2) logP =2.44^(a))  9 CH₂ Cl H

(IB-2) logP = 2.23^(b))  10 CH₂ Br H C₂H₅ OC₂H₅ (IA-3) logP = 2.68^(a)) 11 CH₂ F H OC₂H₅ CH₃ (IA-3) logP = 1.73^(a))  12 CH₂ F H SCH₃ CH₃(IA-3) logP = 1.99^(a))  13 CH₂ F H SO₂CH₃ CH₃ (IA-3) logP = 1.83^(a)) 14 CH₂ Br H CH₃ CH₃ (IB-2) logP = 1.57^(a))  15 CH₂ Br H OC₂H₅ CH₃(IB-2) m.p.: 132° C.  16 CH₂ Br H

(IB-2) logP = 2.31^(a))  17 CH₂ Cl H OC₂H₅

(IA-3) logP = 3.03^(a))  18 CH₂ Cl H CF₃ CH₃ (IA-3) logP = 2.75^(a))  19CH₂ Cl H C₂H₅ OC₂H₅ (IA-3) logP = 2.60^(a))  20 CH₂ NO₂ H SCH₃ CH₃(IA-3) logP = 2.04^(a))  21 CH₂ CF₃ H OC₂H₅

(IA-3) logP = 3.02^(a))  22 CH₂ CF₃ H C₂H₅ OC₂H₅ (IA-3) logP = 2.91^(a)) 23 CH₂ CF₃ H SCH₃ CH₃ (IA-3) logP = 2.59^(a))  24 CH₂ OCH₃ H OC₂H₅ CH₃(IA-3) logP = 1.99^(a))  25 CH₂ OCH₃ H C₂H₅ OC₂H₅ (IA-3) logP =2.18^(a))  26 CH₂ Br H OC₂H₅ CH₃ (IA-3) logP = 2.46^(a))  27 CH₂ Br HCF₃ CH₃ (IA-3) logP = 2.85^(a))  28 CH₂ H H CF₃ CH₃ (IA-3) logP =2.33^(a))  29 CH₂ CF₃ H OCH₃ CH₃ (IA-3) logP = 2.35^(a))  30 CH₂ F H CF₃CH₃ (IA-3) logP = 2.47^(a))  31 CH₂ F H C₂H₅ OC₂H₅ (IA-3) logP =2.28^(a))  32 CH₂ F H OCH₃ CH₃ (IA-3) logP = 1.76^(a))  33 CH₂ H H OC₂H₅CH₃ (IA-3) logP = 1.93^(a))  34 CH₂ H H OCH₃ CH₃ (IA-3) logP = 1.61^(a)) 35 — H (2) CF₃ CF₃ CH₃ (IC-2) m.p.: 190° C.  36 — H H CF₃ CH₃ (IA-3)logP = 2.48^(a))  37 — Cl H CF₃ CH₃ (IA-3) logP = 2.83^(a))  38 — H (2)Cl CH₃ CH₃ (IC-2) m.p.: 196° C.  39 CH₂ Cl (2) Cl CF₃ CH₃ (IB-2) logP =2.79^(a))  40 — Br H CF₃ CH₃ (IA-3) logP = 2.90^(a))  41 CH₂ Cl (2) ClSCH₃ CH₃ (IB-2) logP = 2.38^(a))  42 CH₂ Cl (2) Cl OC₂H₅ CH₃ (IB-2) logP= 2.48^(a))  43 CH₂ Cl (2) Cl

(IB-2) logP = 2.62^(a))  44 CH₂ Cl (2) Cl OCH₃ CH₃ (IB-2) logP =2.14^(a))  45 CH₂ Cl (2) Cl OC₃H₇-i CH₃ (IB-2) logP = 2.79^(a))  46 CH₂Cl (2) Cl OCH₂CF₃ CH₃ (IB-2) logP = 2.84^(a))  47 CH₂ Cl (2) Cl Br CH₃(IB-2) logP = 2.26^(a))  48 CH₂ Cl (2) Cl H CH₃ (IB-2) logP = 1.69^(a)) 49 CH₂ Cl (2) Cl

CH₃ (IB-2) logP = 2.25^(a))  50 CH₂ Cl (2) Cl N(CH₃)₂ CH₃ (IB-2) logP =2.18^(a))  51 CH₂ Cl (2) Cl CH₃ CH₃ (IB-2) logP = 1.79^(a))  52 CH₂ Cl(2) Cl R⁵ + R⁶: (CH₂)₄ (IB-2) logP = 1.98^(a))  53 CH₂ Cl (2) Cl OCH₃

(IB-2) logP = 2.45^(a))  54 CH₂ Cl (2) Cl OC₂H₅

(IB-2) logP = 2.79^(a))  55 CH₂ Cl (2) Cl OC₃H₇-i

(IB-2) logP = 3.14^(a))  56 CH₂ Cl (2) Cl OCH₂CF₃

(IB-2) logP = 3.18^(a))  57 CH₂ Cl (2) Cl SCH₃

(IB-2) logP = 2.77^(a))  58 CH₂ Cl (2) Cl N(CH₃)₂

(IB-2) logP = 2.49^(a))  59 CH₂ Cl (2) Cl CH₃

(IB-2) logP = 2.09^(a))  60 CH₂ Cl (2) Cl C₂H₅ OC₂H₅ (IB-2) logP =2.65^(a))  61 CH₂ CF₃ H CF₃ CH₃ (IA-3) logP = 3.06^(a))  62 CH₂ H H C₂H₅OC₂H₅ (IA-3) logP = 2.10^(a))  63 CH₂ H H SCH₃ CH₃ (IA-3) logP =1.85^(a))  64 CH₂ H H

(IA-3) logP = 2.09^(a))  65 CH₂ Cl (5) Cl CF₃ CH₃ (IA-3) logP =3.24^(a))  66 CH₂ H H SO₂CH₃ CH₃ (IA-3) logP = 1.71^(a))  67 CH₂ SO₂CH₃H OC₂H₅ CH₃ (IA-3) logP = 1.64^(a))  68 CH₂ Br H R⁷ + R⁶: (CH₂)₄ (IA-3)logP = 1.64^(a))  69 CH₂ Br H OC₃H₇-n CH₃ (IA-3) logP = 2.82^(a))  70CH₂ Br H OC₃H₇-i CH₃ (IA-3) logP = 2.84^(a))  71 CH₂ CF₃ H OC₃H₇-i CH₃(IA-3) logP = 3.05^(a))  72 CH₂ CF₃ H OC₃H₇-n CH₃ (IA-3) logP =3.06^(a))  73 CH₂ Br H Br CH₃ (IA-3) logP = 2.33^(a))  74 CH₂ CF₃ HOC₃H₇-i

(IA-3) logP = 3.38^(a))  75 CH₂ CF₃ H CH₂OCH₃

(IA-3) logP = 2.53^(a))  76 CH₂ CF₃ H CH₂OCH₃ CH₃ (IA-3) logP =2.26^(a))  77 CH₂ I H CF₃ CH₃ (IA-3) logP = 2.98^(a))  78 CH₂ Br H SCH₃CH₃ (IA-3) logP = 2.36^(a))  79 CH₂ Cl H SCH₃ CH₃ (IA-3) logP =2.30^(a))  80 CH₂ CF₃ H CH₃ CH₃ (IA-3) logP = 2.06^(a))  81 CH₂ CF₃ HOC₂H₅ C₂H₅ (IA-3) logP = 3.01^(a))  82 CH₂ CF₃ H N(CH₃)₂ CH₃ (IA-3) logP= 2.40^(a))  83 CH₂ CF₃ H Br CH₃ (IA-3) logP = 2.54^(a))  84 CH₂ H (3)CH₃ OC₂H₅ CH₃ (IA-3) logP = 2.21^(a))  85 CH₂ Br H

(IA-3) logP = 2.62^(a))  86 CH₂ Br H

CH₃ (IA-3) logP = 2.99^(a))  87 CH₂ CF₃ H SC₂H₅ CH₃ (IA-3) logP =2.94^(a))  88 CH₂ CF₃ H SC₃H₇-i CH₃ (IA-3) logP = 2.63^(a))  89 CH₂ CF₃H R⁵ + R⁶: (CH₂)₄ (IA-3) logP = 2.25^(a))  90 CH₂ CF₃ H OCH₃

(IA-3) logP = 2.65^(a))  91 CH₂ CF₃ H OCH₂CF₃ CH₃ (IA-3) logP =3.06^(a))  92 CH₂ CN H CF₃ CH₃ (IA-3) logP = 2.29^(a))  93 CH₂ F HN(CH₃)₂ CH₃ (IA-3) logP = 1.81^(a))  94 CH₂ F H OC₃H₇-n CH₃ (IA-3) logP= 2.44^(a))  95 CH₂ F H CH₂OCH₃ CH₃ (IA-3) logP = 1.69^(a))  96 CH₂ F HOCH₃

(IA-3) logP = 2.05^(a))  97 CH₂ F H OC₂H₅

(IA-3) logP = 2.39^(a))  98 CH₂ I H OC₂H₅ CH₃ (IA-3) logP = 2.59^(a)) 99 CH₂ OCH₃ (2) NO₂ OC₂H₅ CH₃ (IC-2) logP = 2.24^(a)) 100 CH₂ OCH₃ (2)NO₂ SCH₃ CH₃ (IC-2) logP = 2.18^(a))

TABLE 2 Examples of compounds of the formula (ID) (position) (position)(position) (position) Ex. No. A R¹ (R²)_(m) R³ (R⁴)_(n) (position) Zphysical data ID-1 CH₂ H H (2) Cl (4) Cl

logP = 4.26^(a)) ID-2 CH₂ (5) CH₃ (5) CH₃ (4) CF₃ H

logP = 2.61^(a)) ID-3 CH₂ H H (4) CF₃ H

logP = 2.24^(a)) ID-4 CH₂ H H (4) CF₃ H

logP = 2.63^(a)) ID-5 CH₂ H H H H

logP = 2.35^(a)) ID-6 CH₂ H H (4) CF₃ H

logP = 3.77^(a)) ID-7 CH₂ (5) CH₃ (5) CH₃ (4) CF₃ H

logP = 3.27^(a)) ID-8 CH₂ (5) CH₃ (5) CH₃ (4) CF₃ H

logP = 3.18^(a)) ID-9 CH₂ H H (4) Br H

logP = 2.92^(a)) ID-10 CH₂ H H (4) Br H

logP = 3.04^(a)) ID-11 CH₂ (5) CH₃ (5) CH₃ (2) Cl (4) Cl

m.p.: 140° C. logP = 2.72^(a)) ID-12 CH₂ (5) CH₃ (5) CH₃ (2) Cl (4) Cl

m.p.: 103° C. logP = 3.08^(a)) ID-13 CH₂ (5) CH₃ (5) CH₃ (2) Cl (4) Cl

m.p.: 118° C. logP = 2.98^(a)) ID-14 CH₂ (5) CH₃ (5) CH₃ (2) Cl (4) Cl

m.p.: 132° C. logP = 2.32^(a)) ID-15 CH₂ (5) CH₃ (5) CH₃ (2) Cl (4) Cl

m.p.: 170° C. logP = 2.86^(a)) ID-16 CH₂ (4) CH₃ (4) CH₃ (2) Cl (4) Cl

logP = 2.78^(a)) ID-17 CH₂ (4) CH₃ (4) CH₃ (2) Cl (4) Cl

logP = 3.15^(a)) ID-18 CH₂ (4) CH₃ (4) CH₃ (2) Cl (4) Cl

logP = 3.06^(a)) ID-19 CH₂ (4) CH₃ (4) CH₃ (2) Cl (4) Cl

logP = 2.38^(a)) ID-20 CH₂ (4) CH₃ (4) CH₃ (2) Cl (4) Cl

logP = 2.94^(a)) ID-21 CH₂ (5) C₃H₇-i H (2) Cl (4) Cl

logP = 3.12^(a)) ID-22 CH₂ (5) C₃H₇-i H (2) Cl (4) Cl

logP = 3.49^(a)) ID-23 CH₂ (5) C₃H₇-i H (2) Cl (4) Cl

logP = 3.39^(a)) ID-24 CH₂ (5) C₃H₇-i H (2) Cl (4) Cl

logP = 2.70^(a)) ID-25 CH₂ (5) C₃H₇-i H (2) Cl (4) Cl

logP = 3.28^(a)) ID-26 CH₂ (5) CH₃ H (2) Cl (4) Cl

ID-27 CH₂ (5) CH₃ H (2) Cl (4) Cl

ID-28 CH₂ (5) CH₃ H (2) Cl (4) Cl

ID-29 CH₂ (5) CH₃ H (2) Cl (4) Cl

ID-30 CH₂ (5) CH₃ H (2) Cl (4) Cl

Starting Materials of Formula (III):

Example (III-1)

4.5 g (15 mmol) of2-(3-chloro-4-cyano-phenyl)-4-methyl-5-trifluoromethyl-2.4-dihydro-3H-1,2,4-triazol-3-oneare taken up in 80 ml of 60% strength sulphuric acid, and the mixture isheated under reflux for 6 hours. After cooling to room temperature, theresulting crystalline produce is isolated by filtration with suction.

This gives 4.5 g (91% of theory) of2-(3-carboxy-4-chloro-phenyl)₄-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 223° C.

Example (III-2)

2 g (4.9 mmol) of5-bromo-4-methyl-2-(2-ethoxycarbonyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one(compare Example IV-1) are dissolved in 30 ml of 10% strength ethanolicpotassium hydroxide solution and heated under reflux for 2 hours. Thereaction mixture is concentrated under water pump vacuum, taken up in 20ml of water and acidified with dilute hydrochloric acid. The solid thatprecipitates out is filtered and dried.

This gives 1.2 g (71% of theory) of5-ethoxy-4-methyl-2-(2-carboxy-5-trifluoro-methyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneas a solid product.

logP: 2.18^(a))

Example (III-3)

13.4 g (35 mmol)4-methyl-5-trifluoromethyl-2-(2,6-dichloro-3-methoxycarbonyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneare initially charged in 60 ml of 1,4-dioxane, and a solution of 1.54 g(38,5 mmol) of sodium hydroxide in 20 ml of water is slowly metered inat room temperature. The reaction mixture is stirred at 60° C. for 150minutes and subsequently concentrated under water pump vacuum. Theresidue is dissolved in 100 ml of water, and the pH of the solution isadjusted to 1 by addition of conc. hydrochloric acid. The resultingcrystalline product is isolated by filtration with suction.

This gives 11.7 g (90% of theory) of4-methyl-5-trifluoromethyl-2-(2,6-dichloro-3-carboxy-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 207° C.

By the methods of Examples (III-1) and (III-3), it is also possible toprepare, for example, the compounds of the general formula (III) listedin Table 2 below.

TABLE 2 Examples of compounds of the formula (III) (position-)(position-) Ex. No. R³ (R⁴)_(n) (position-) -A-Z physical data III-4(4-) Cl H

logP = 1.39^(a)) III-5 (4-) SO₂CH₃ H

logP = 1.47^(a)) III-6 (4-) F H

logP = 1.73^(a)) III-7 (4-) CF₃ H

logP = 1.65^(a)) III-8 (4-) Br H

logP = 1.74^(a)) III-9 (4-) CF₃ H

logP = 2.43^(a)) III-10 (4-) CF₃ H

logP = 2.12^(a)) III-11 (4-) CF₃ H

logP = 1.61^(a)) III-12 (4-) CF₃ H

logP = 1.93^(a)) III-13 (4-) CF₃ H

logP = 2.01^(a)) III-14 (4-) CF₃ H

logP = 1.77^(a)) III-15 (3-) CH₃ H

logP = 1.70^(a)) III-16 (4-) SO₂CH₃ H

logP = 1.07^(a)) III-17 (4-) CF₃ H

logP = 2.35^(a)) III-18 (4-) CF₃ H

logP = 2.63^(a)) III-19 (4-) CF₃ H

logP = 2.13^(a)) III-20 (4-) CF₃ H

logP = 1.82^(a)) III-21 (4-) CF₃ H

logP = 2.48^(a)) III-22 (4-) CF₃ H

logP = 1.73^(a)) III-23 (4-) CF₃ H

logP = 3.11^(a)) III-24 (4-) F H

logP = 1.43^(a)) III-25 (4-) F H

logP = 1.97^(a)) III-26 (4-) F H

logP = 1.30^(a)) III-27 (4-) F H

logP = 1.63^(a)) III-28 (4-) F H

logP = 1.93^(a)) III-29 (4-) CF₃ H

logP = 1.78^(a)) III-30 (2-) Cl (4-) Cl

m.p.: 230° C. logP = 1.63^(a)) III-31 (2-) Cl (4-) Cl

m.p.: 190° C. logP = 1.73^(a)) III-32 (2-) Cl (4-) Cl

m.p.: 210° C. logP = 1.87^(a)) III-33 (2-) Cl (4-) Cl

m.p.: 210° C. logP = 1.43^(a)) III-34 (2-) Cl (4-) Cl

m.p.: 164° C. logP = 2.01^(a)) III-35 (2-) Cl (4-) Cl

m.p.: 168° C. logP = 2.04^(a)) III-36 (2-) Cl (4-) Cl

m.p.: 218° C. logP = 1.53^(a)) III-37 (2-) Cl (4-) Cl

m.p.: 259° C. logP = 0.98^(a)) III-38 (2-) Cl (4-) Cl

m.p.: 210° C. logP = 1.56^(a)) III-39 (2-) Cl (4-) Cl

m.p.: 197° C. logP = 1.51^(a)) III-40 (2-) Cl (4-) Cl

m.p.: 262° C. logP = 1.11^(a)) III-41 (2-) Cl (4-) Cl

m.p.: 249° C. logP = 1.30^(a)) III-42 (2-) Cl (4-) Cl

m.p.: 200° C. logP = 1.71^(a)) III-43 (2-) Cl (4-) Cl

m.p.: 189° C. logP = 2.01^(a)) III-44 (2-) Cl (4-) Cl

m.p.: 178° C. logP = 2.28^(a)) III-45 (2-) Cl (4-) Cl

m.p.: 161° C. logP = 2.31^(a)) III-46 (2-) Cl (4-) Cl

m.p.: 200° C. logP = 1.98^(a)) III-47 (2-) Cl (4-) Cl

m.p.: 201° C. logP = 1.39^(a)) III-48 (2-) Cl (4-) Cl

m.p.: 207° C. logP = 1.77^(a)) III-49 (2-) Cl (4-) Cl

m.p.: 140° C. logP = 1.88^(a)) III-50 (4-) OCH₂CHF₂ H

m.p.: 154° C. logP = 2.14^(a)) III-51 H H

m.p.: 214° C. logP = 1.87^(a)) III-52 H H

m.p.: 194° C. logP = 2.07^(a)) III-53 H H

m.p.: 181° C. logP = 1.97^(a)) III-54 H H

m.p.: 251° C. logP = 1.14^(a)) III-55 (2-) Cl (4-) Cl

logP = 1.38^(a)) III-56 (2-) Cl (4-) Cl

logP = 1.48^(a)) III-57 (2-) Cl (4-) Cl

III-58 (4-) Cl H

¹H NMR (DMSO-D6, δ): 5.42 ppm. III-59 (4-) CF₃ H

¹H NMR (DMSO-D6, δ): 5.48 ppm. III-60 (4-) CF₃ H

¹H NMR (DMSO-D6, δ): 5.60 ppm. LogP = 2.47^(a)) III-61 (4-) CF₃ H

logP = 2.33^(a)) III-62 (4-) SO₂CH₃ H

¹H NMR (DMSO-D6, δ): 5.14 ppm. III-63 (4-) SO₂CH₃ H

¹H NMR (DMSO-D6, δ): 5.27 ppm. III-64 (4-) Cl H

¹H NMR (CDCl₃, δ): 5.12 ppm. III-65 (4-) Cl H

¹H NMR (DMSO-D6, δ): 5.20 ppm. III-66 (4-) Cl H

¹H NMR (DMSO-D6, δ): 5.03 ppm. III-67 (4-) Br H

¹H NMR (DMSO-D6, δ): 5.24 ppm. III-68 (4-) Br H

¹H NMR (DMSO-D6, δ): 5.39 ppm. III-69 (4-) F H

¹H NMR (DMSO-D6, δ): 5.19 ppm. III-70 (4-) F H

¹H NMR (DMSO-D6, δ): 5.30 ppm. III-71 (4-) F H

¹H NMR (DMSO-D6, δ): 5.43 ppm. III-72 (4-) Br H

¹H NMR (CDCl₃, δ): 5.10 ppm. III-73 (4-) Br H

¹H NMR (DMSO-D6, δ): 5.03 ppm. III-74 (4-) Br H

¹H NMR (DMSO-D6, δ): 5.19 ppm. III-75 (4-) Br H

¹H NMR (DMSO-D6, δ): 5.01 ppm. III-76 (4-) Cl H

¹H NMR (DMSO-D6, δ): 5.14 ppm. III-77 (4-) Cl H

¹H NMR (DMSO-D6, δ): 5.25 ppm. III-78 (4-) NO₂ H

¹H NMR (DMSO-D6, δ): 5.23 ppm. III-79 (4-) NO₂ H

¹H NMR (DMSO-D6, δ): 5.37 ppm. III-80 (4-) CF₃ H

logP = 2.46^(a)) III-81 (4-) CF₃ H

¹H NMR (DMSO-D6, δ): 5.31 ppm. III-82 (4-) CF₃ H

logP = 2.08^(a)) III-83 (4-) OCH₃ H

¹H NMR (CDCl₃, δ): 5.38 ppm. III-84 (4-) OCH₃ H

¹H NMR (CDCl₃, δ): 5.43 ppm. III-85 (4-) CF₃ H

¹H NMR (CDCl₃, δ): 5.47 ppm. III-86 (4-) Br H

LogP = 1.44^(a)) III-87 (4-) Br H

LogP = 1.63^(a)) III-88 (4-) Br H

LogP = 2.27^(a)) III-89 (4-) Br H

LogP = 2.31^(a)) III-90 H H

LogP = 1.82^(a)) III-91 (4-) Br H

¹H NMR (CDCl₃, δ): 5.32 ppm. III-92 (4-) Br H

¹H NMR (CDCl₃, δ): 5.53 ppm. III-93 (4-) F H

^(1H NMR (CDCl) ₃, δ): 5.39 ppm. III-94 (4-) F H

¹H NMR (CDCl₃, δ): 5.57 ppm. III-95 (4-) F H

¹H NMR (CDCl₃, δ): 5.44 ppm. III-96 (4-) F H

¹H NMR (CDCl₃, δ): 5.41 ppm. III-97 H H

¹H NMR (CDCl₃, δ): 5.34 ppm. III-98 H H

¹H NMR (CDCl₃, δ): 5.38 ppm. III-99 H H

¹H NMR (CDCl₃, δ): 5.26 ppm. III-100 H H

¹H NMR (CDCl₃, δ): 5.43 ppm. III-101 H H

LogP = 1.23^(a)) III-102 (4-) SO₂CH₃ H

logP = 1.14^(a)) III-103 (4-) CF₃ H

logP = 2.45^(a)) III-104 (4-) CF₃ H

logP = 2.48^(a)) III-105 (4-) Br H

logP = 1.85^(a)) III-106 (4-) CF₃ H

logP = 2.74^(a)) III-107 (4-) CF₃ H

logP = 2.01^(a)) III-108 (4-) CF₃ H

logP = 1.79^(a)) III-109 (4-) CF₃ H

logP = 1.65^(a)) III-110 (4-) Br H

logP = 1.90^(a)) III-111 (4-) Cl H

logP = 1.83^(a)) III-112 (4-) I H

logP = 2.06^(a)) III-113 (4-) I H

III-114 (4-) Br H

m.p.: 191° C. III-115 (4-) Br H

m.p.: 213° C. III-116 H H

III-117 H H

m.p.: 112° C. III-118 (4-) CF₃ H

m.p.: 158° C. III-119 (4-) CF₃ H

m.p.: 162° C. III-120 (4-) Cl (5-) Cl

m.p.: 167° C. III-121 H H

m.p.: 188° C. III-122 H H

III-123 H H

m.p.: 131° C. III-124 (4-) Cl H

m.p.: 109° C. III-125 (4-) I H

m.p.: 104° C. III-126 (4-) Br H

m.p.: 99° C. III-127 (4-) Br H

m.p.: 174° C. III-128 H H

m.p.: 122° C. III-129 (4-) Br H

m.p.: 164° C. III-130 H H

m.p.: 154° C. III-131 (4-) Br H

m.p.: 161° C. III-132 (4-) CN H

m.p.: 196° C. III-133 H H

m.p.: 192° C. III-134 H H

III-135 (4-) Br H

m.p.: 252° C. III-136 (2-) NO₂ (3-) OCH₃

logP = 1.65^(a)) III-137 (2-) NO₂ (3-) OCH₃

logP = 1.58^(a))Starting Materials of the Formula (IV):

Example (IV-1)

10 g (49 mmol) of 2-methyl-4-trifluoromethyl-benzoic acid are dissolvedin 150 ml of ethanol and admixed with 1 ml of conc. sulphuric acid. Thesolution is heated under reflux for 24 hours and then concentrated, andthe residue is taken up in methylene chloride and extracted withsaturated aqueous sodium bicarbonate solution. The methylene chloridephase is dried over sodium sulphate and concentrated under water pumpvacuum.

This gives 9 g (80% of theory) of ethyl2-methyl-4-trifluoromethyl-benzoate as an amorphous residue.

9 g (39 mmol) of ethyl 2-methyl-4-trifluoromethyl-benzoate are dissolvedin 200 ml of tetrachloromethane and admixed with 7 g (39 mmol) ofN-bromo-succinimide and 0.1 g of dibenzoyl peroxide. The mixture isheated under reflux for 6 hours, and the precipitated succinimide isthen filtered off and the filtrate is concentrated under water pumpvacuum.

This gives 12 g of an amorphous residue which, in addition to ethyl2-bromomethyl-4-trifluoromethyl-benzoate, contains 17% of ethyl2,2-dibromomethyl-4-trifluoromethyl-benzoate and 12% of ethyl2-methyl-4-trifluoromethyl-benzoate.

4 g of ethyl 2-bromomethyl-4-trifluoromethyl-benzoate (approximately 70%pure) and 2.28 g (12.8 mmol) of5-bromo-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 150ml of acetonitrile, admixed with 5.3 g (38.4 mmol) of potasssiumcarbonate and heated under reflux with vigoruous stirring for 2 hours.The reaction mixture is taken up in water and extracted repeatedly withmethylene chloride. The combined methylene chloride phases are driedover sodium sulphate, concentrated under water pump vacuum andchromatographed.

This gives 2 g (38% of theory) of5-bromo-4-methyl-2-(2-ethoxycarbonyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneas an amorphous product.

¹H-NMR (CDCl₃, δ): 5.46 ppm.

Example (IV-2)

6.7 g (40 mmol) of4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one areinitially charged in 150 ml of acetonitrile and admixed with 11 g (80mmol) of potassium carbonate. The mixture is heated to 50° C., and asolution of 13.1 g (44 mmol) of methyl3-bromomethyl-2,4-dichloro-benzoate in 20 ml of acetonitrile is thenadded dropwise with stirring, and the reaction mixture is heated underreflux with stirring for another 15 hours. The mixture is subsequentlyconcentrated under water pump vacuum, and the residue is taken up inmethylene chloride, washed with 1N hydrochloric acid, dried with sodiumsulphate and filtered. The filtrate is concentrated under reducedpressure, the residue is digested with petroleum ether and thecrystalline product is isolated by filtration with suction.

This gives 14.9 g (97% of theory) of4-methyl-5-trifluoromethyl-2-(2,6-dichloro-3-methoxycarbonyl-benzyl)-2,4-dihydro-3H-1.2.4-triazol-3-oneof melting point 109° C.

By the methods of Examples (IV-1) and (IV-2), it is also possible toprepare, for example, the compounds of the general formula (IVa) listedin Table 3 below.

TABLE 3 Examples of compounds of the formula (IV) (position-)(position-) Ex. No. R³ (R⁴)_(n) (position-) —A—Z X physical data IV-3(2-) Cl (4-) Cl

OCH₃ m.p.: 229° C. logP = 2.27^(a)) IV-4 (2-) Cl (4-) Cl

OCH₃ m.p.: 120° C. logP = 2.38^(a)) IV-5 (2-) Cl (4-) Cl

OCH₃ m.p.: 127° C. logP = 2.55^(a)) IV-6 (2-) Cl (4-) Cl

OCH₃ m.p.: 121° C. logP = 2.04^(a)) IV-7 (2-) Cl (4-) Cl

OCH₃ m.p.: 68° C. logP = 2.73^(a)) IV-8 (2-) Cl (4-) Cl

OCH₃ m.p.: 129° C. logP = 2.72^(a)) IV-9 (2-) Cl (4-) Cl

OCH₃ m.p.: 164° C. logP = 2.18^(a)) IV-10 (2-) Cl (4-) Cl

OCH₃ m.p.: 158° C. logP = 1.55^(a)) IV-11 (2-) Cl (4-) Cl

OCH₃ m.p.: 106° C. logP = 2.16^(a)) IV-12 (2-) Cl (4-) Cl

OCH₃ m.p.: 126° C. logP = 2.11^(a)) IV-13 (2-) Cl (4-) Cl

OCH₃ m.p.: 146° C. logP = 1.65^(a)) IV-14 (2-) Cl (4-) Cl

OCH₃ m.p.: 178° C. logP = 1.86^(a)) IV-15 (2-) Cl (4-) Cl

OCH₃ m.p.: 97° C. logP = 2.36^(a)) IV-16 (2-) Cl (4-) Cl

OCH₃ m.p.: 99° C. logP = 2.73^(a)) IV-17 (2-) Cl (4-) Cl

OCH₃ m.p.: 56° C. logP = 3.08^(a)) IV-18 (2-) Cl (4-) Cl

OCH₃ m.p.: 102° C. logP = 3.05^(a)) IV-19 (2-) Cl (4-) Cl

OCH₃ m.p.: 131° C. logP = 2.70^(a)) IV-20 (2-) Cl (4-) Cl

OCH₃ m.p.: 135° C. logP = 1.97^(a)) IV-21 (2-) Cl (4-) Cl

OCH₃ m.p.: 143° C. logP = 2.42^(a)) IV-22 (2-) Cl (4-) Cl

OCH₃ m.p.: 85° C. logP = 2.58^(a)) IV-23 (2-) Cl (4-) Cl

OCH₃ logP = 1.98^(a)) IV-24 (2-) Cl (4-) Cl

OCH₃ logP = 2.07^(a)) IV-25 (2-) Cl (4-) Cl

OCH₃ m.p.: 157° C. logP = 2.94^(a)) IV-26 (4-) CF₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.53 ppm. IV-27 (4-) NO₂ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.48 ppm. IV-28 (4-) NO₂ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.30 ppm. IV-29 (4-) SO₂CH₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.61 ppm. IV-30 (4-) Cl H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.08 ppm. IV-31 (4-) Cl H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.17 ppm. IV-32 (4-) Cl H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.00 ppm. IV-33 (4-) SO₂CH₃ H

OC₂H₅ logP = 1.53^(a)) IV-34 (4-) Br H

OC₂H₅ logP = 3.24^(a)) IV-35 (4-) Br H

OC₂H₅ logP = 3.40^(a)) IV-36 (4-) F H

OC₂H₅ logP = 2.41^(a)) IV-37 (4-) F H

OC₂H₅ logP = 2.45^(a)) IV-38 (4-) Br H

OC₂H₅ logP = 2.06^(a)) IV-39 (4-) Br H

OC₂H₅ logP = 2.64^(a)) IV-40 (4-) Br H

OC₂H₅ logP = 3.23^(a)) IV-41 (4-) Br H

OC₂H₅ logP = 3.02^(a)) IV-42 (4-) Cl H

OC₂H₅ logP = 3.23^(a)) IV-43 (4-) Cl H

OC₂H₅ logP = 3.31^(a)) IV-44 (4-) Cl H

OC₂H₅ logP = 3.14^(a)) IV-45 (4-) NO₂ H

OC₂H₅ logP = 2.42^(a)) IV-46 (4-) NO₂ H

OC₂H₅ logP = 2.82^(a)) IV-47 (4-) CF₃ H

OC₂H₅ logP = 3.48^(a)) IV-48 (4-) CF₃ H

OC₂H₅ logP = 3.38^(a)) IV-49 (4-) CF₃ H

OC₂H₅ logP = 3.02^(a)) IV-50 (4-) CF₃ H

OC₃H₇ logP = 3.91^(a)) IV-51 (4-) OCH₃ H

OC₂H₅ IV-52 (4-) OCH₃ H

OC₂H₅ IV-53 (4-) CF₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.37 ppm. IV-54 (4-) CF₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.37 ppm. IV-55 H H

OC₂H₅ IV-56 H H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.37 ppm. IV-57 H H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.40 ppm. IV-58 (4-) Br H

OC₂H₅ logP = 2.95^(a)) IV-59 (4-) Br H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.31 ppm. IV-60 (4-) Br H

OC₂H₅ logP = 2.44^(a)) IV-61 (4-) F H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.35 ppm. IV-62 (4-) F H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.53 ppm. IV-63 (4-) F H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.40 ppm. IV-64 (4-) F H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.36 ppm. IV-65 (4-) Br H

OC₂H₅ logP = 3.34^(a)) IV-66 (4-) Br H

OC₂H₅ logP = 3.38^(a)) IV-67 (4-) Br H

OC₂H₅ logP = 3.31^(a)) IV-68 (4-) Br H

OC₂H₅ logP = 2.16^(a)) IV-69 (4-) Br H

OC₂H₅ logP = 2.41^(a)) IV-70 (4-) CF₃ H

OC₂H₅ logP = 3.51^(a)) IV-71 (4-) CF₃ H

OC₂H₅ logP = 3.54^(a)) IV-72 (4-) Br H

OC₂H₅ logP = 2.36^(a)) IV-73 (4-) Br H

OC₂H₅ logP = 2.88^(a)) IV-74 (4-) CF₃ H

OC₂H₅ logP = 2.68^(a)) IV-75 (4-) Br H

OC₂H₅ logP = 2.80^(a)) IV-76 (4-) CF₃ H

OC₂H₅ logP = 3.87^(a)) IV-77 (4-) CF₃ H

OC₂H₅ logP = 2.88^(a)) IV-78 (4-) CF₃ H

OC₂H₅ logP = 2.60^(a)) IV-79 (4-) CF₃ H

OC₂H₅ logP = 3.35^(a)) IV-80 (4-) Br H

OC₂H₅ logP = 2.86^(a)) IV-81 (4-) Cl H

OC₂H₅ logP = 2.83^(a)) IV-82 (4-) Br H

OC₂H₅ logP = 2.60^(a)) IV-83 (4-) CF₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.36 ppm. IV-84 (4-) CF₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.37 ppm. IV-85 (4-) CF₃ H

OC₂H₅ logP = 2.79^(a)) IV-86 (4-) CF₃ H

OC₂H₅ logP = 3.67^(a)) IV-87 (4-) CF₃ H

OC₂H₅ logP = 3.80^(a)) IV-88 (3-) CH₃ H

OC₂H₅ logP = 2.54^(a)) IV-89 (4-) SO₂CH₃ H

OC₂H₅ logP = 1.82^(a)) IV-90 (4-) CF₃ H

OC₂H₅ logP = 2.93^(a)) IV-91 (4-) CF₃ H

OC₂H₅ logP = 3.08^(a)) IV-92 (4-) CF₃ H

OC₂H₅ logP = 3.04^(a)) IV-93 (4-) CF₃ H

OC₂H₅ logP = 3.45^(a)) IV-94 (4-) F H

OC₂H₅ logP = 2.21^(a)) IV-95 (4-) F H

OC₂H₅ logP = 2.96^(a)) IV-96 (4-) F H

OC₂H₅ logP = 2.05^(a)) IV-97 (4-) F H

OC₂H₅ logP = 2.50^(a)) IV-98 (4-) F H

OC₂H₅ logP = 2.89^(a)) IV-99 (4-) CF₃ H

OC₂H₅ logP = 2.91^(a)) IV-100 (4-) Cl H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.39 ppm. IV-101 (4-) Cl H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.50 ppm. IV-102 (4-) Cl H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.49 ppm. IV-103 (4-) CF₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.29 ppm. IV-104 (4-) CF₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.53 ppm. IV-105 (4-) CF₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.34 ppm. IV-106 (4-) SO₂CH₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.39 ppm. IV-107 (4-) SO₂CH₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.43 ppm. IV-108 (4-) SO₂CH₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.40 ppm. IV-109 (4-) SO₂CH₃ H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.38 ppm. IV-110 (4-) Br H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.49 ppm. IV-111 H H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.3 ppm. IV-112 H H

OC₂H₅ ¹H NMR (CDCl₃, δ): 5.44 ppm. IV-113 (4-) CF₃ H

OC₂H₅ logP = 2.58^(a)) IV-114 (4-) SO₂CH₃ H

OCH₃ logP = 1.53^(a)) IV-115 (4-) SO₂CH₃ H

OCH₃ logP = 1.59^(a)) IV-116 (4-) I H

OCH₃ logP = 2.68^(a)) IV-117 (4-) CF₃ H

OCH₃ logP = 2.74^(a)) IV-118 (4-) CF₃ H

OCH₃ logP = 2.65^(a)) IV-119 (4-) CF₃ H

OC₂H₅ logP = 2.96^(a)) IV-120 H H

OCH₃ m.p.: 106° C. IV-121 (2-) NO₂ (3-) OCH₃

OCH₃ logP = 2.27^(a)) IV-122 (2-) NO₂ (3-) OCH₃

OCH₃ logP = 2.19^(a))

The logP values given in the Tables were determined in accordance withEEC Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reversed-phase column (C 18). Temperature: 43°C.

-   (a) Mobile phases for the determination in the acidic range: 0.1%    aqueous phosphoric acid, acetonitrile; linear gradient from 10%    acetonitrile to 90% acetonitrile—the corresponding data in the    Tables are labelled ^(a)).-   (b) Mobile phases for the determination in the neutral range:    0.01-molar aqueous phosphate buffer solution, acetonitrile; linear    gradient from 10% acetonitrile to 90% acetonitrile—the corresponding    data in the Tables are labelled ^(b)).

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) whose logP values are known (determination of the logPvalues using the retention times by linear interpolation between twosuccessive alkanones).

The lambda-max values were determined using the UV spectra from 200 nmto 400 nm in the maxima of the chromatographic signals.

Use Examples Example A

Pre-emergence test

-   Solvent: 5 parts by weight of acetone-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After approximately 24hours, the soil is sprayed with the preparation of active compound suchthat the particular amount of active compound desired is applied perunit area. The concentration of the spray liquor is chosen so that theparticular amount of active compound desired is applied in 1000 litersof water per hectare.

After three weeks, the degree of damage to the plants is assesssed in %damage in comparison to the development of the untreated control.

The figures denote:

 0% = no effect (like untreated control) 100% = total destruction

In this test, for example the compounds of Preparation Example 1 and 10exhibit strong activity against weeds, and some of them are toleratedwell by crop plants, such as, for example, maize.

TABLE A Pre-emergence test/greenhouse Active compound of PreparationExample No. Amount used (g ai./ha) Maize Cyperus Abutilon

1000 — 100 100

500 0 100 90

Example B

Post-Emergence Test

-   Solvent: 5 parts by weight of acetone-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of active compound in such a way that the particular amountsof active compound desired are applied per unit area. The concentrationof the spray liquor is chosen so that the particular amounts of activecompound desired are applied in 1000 1 of water/ha.

After three weeks, the degree of damage to the plants is assesssed in %damage in comparison to the development of the untreated control.

The figures denote:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example the compounds of Preparation Example 10 and 15exhibit strong activity against weeds, and some of them are toleratedwell by crop plants, such as, for example, maize.

TABLE B Post emergence test/greenhouse Active compound of PreparationExample No. Amount used (g ai./ha) Maize Amaranthus Sinapis

500 20 95 80

1000 0 90 80

1. A substituted benzoylcyclohexanedione of the formula (I),

in which m represents the numbers 0, 1, 2 or 3, n represents the numbers0, 1, 2 or 3, A represents a single bond or represents alkanediyl(alkylene), R¹ represents hydrogen or represents unsubstituted orsubstituted alkyl or alkoxycarbonyl, R² represents unsubstituted orsubstituted alkyl, or together with R¹ represents alkanediyl (alkylene)where in this case m represents 1 and R¹ and R² are located at the samecarbon atom (“geminal”) or at two adjacent carbon atoms (“vicinal”), R³represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,halogen, or represents unsubstituted or substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl, R⁴ represents nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents unsubstituted or substitutedalkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,dialkylamino or dialkylaminosulphonyl, and Z represents one of theheterocyclic groupings below

in which the bond drawn broken in each case denotes a single bond or adouble bond, Q represents oxygen, R⁵ represents hydrogen, hydroxyl,mercapto, cyano, halogen, or represents unsubstituted or halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl-orC₁-C₄-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case up to 6 carbon atoms in the alkyl groups, or representsunsubstituted or halogen-substituted alkylamino or dialkylamino havingin each case up to 6 carbon atoms in the alkyl groups, or representsunsubstituted or halogen-substituted alkenyl, alkinyl, alkenyloxy,alkenylthio or alkenylamino having in each case up to 6 carbon atoms inthe alkenyl or alkinyl groups, or represents unsubstituted orhalogen-substituted cycloalkyl, cycloalkylalkyl, cycloalkyloxy,cycloalkylthio or cycloalkylamino having in each case 3 to 6 carbonatoms in the cycloalkyl groups and optionally up to 4 carbon atoms inthe alkyl moiety, or represents unsubstituted or halogen-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino,benzyl, benzyloxy, benzylthio or benzylamino, and R⁶ representshydrogen, hydroxyl, amino, alkylideneamino having up to 4 carbon atoms,or represents unsubstituted or halogen- or C₁-C₄-alkoxy-substitutedalkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in eachcase up to 6 carbon atoms in the alkyl groups, or representsunsubstituted or halogen-substituted alkenyl, alkinyl or alkenyloxyhaving in each case up to 6 carbon atoms in the alkenyl or alkinylgroups, or represents unsubstituted or halogen-substituted cycloalkyl,cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbonatoms in the cycloalkyl groups and optionally up to 3 carbon atoms inthe alkyl moiety, or represents unsubstituted or halogen-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted phenyl or benzyl, or together with anadjacent radical R⁵ or R⁶ represents unsubstituted or halogen- orC₁-C₄-alkyl-substituted alkanediyl having 3 to 5 carbon atoms, or—in thecase that two adjacent radicals R⁵ and R⁵ are located at a doublebond—together with the adjacent radical R⁵ also represents a benzogrouping including all possible tautomeric forms of the substitutedbenzoylcyclohexanedione of the formula (I) and the possible salts of thesubstituted benzoylcyclohexanedione of the formula (I).
 2. A substitutedbenzoylcyclohexanedione according to claim 1, wherein: m represents thenumbers 0, 1 or 2, n represents the numbers 0, 1 or 2, A representsalkanediyl (alkylene) having 1 to 4 carbon atoms, R¹ represents a singlebond or represents hydrogen, or represents unsubstituted or halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms orrepresents alkoxycarbonyl having up to 6 carbon atoms, R² representsunsubstituted or halogen-substituted alkyl having 1 to 6 carbon atoms,or together with R¹ represents alkanediyl (alkylene) having 2 to 5carbon atoms, where in this case m represents 1 and R¹ and R² arelocated at the same carbon atom (“geminal”) or at two adjacent carbonatoms (“vicinal”), R³ represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, represents unsubstituted or halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having up to 4 carbon atoms in thealkyl groups, or represents alkylamino, dialkylamino ordialkylaminosulphonyl having up to 4 carbon atoms in the alkyl groups,R⁴ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen,represents unsubstituted or halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy,alkylthio, alkylsulphinyl or alkylsulphonyl having up to 4 carbon atomsin the alkyl groups, or represents alkylamino, dialkylamino ordialkylaminosulphonyl having up to 4 carbon atoms in the alkyl groups,and Z represents one of the heterocyclic groupings below

in which the bond drawn broken in each case denotes a single bond or adouble bond, Q represents oxygen, R⁵ represents hydrogen, hydroxyl,mercapto, cyano, halogen, or represents unsubstituted or halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl-orC₁-C₄-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case up to 6 carbon atoms in the alkyl groups, or representsunsubstituted or halogen-substituted alkylamino or dialkylamino havingin each case up to 6 carbon atoms in the alkyl groups, or representsunsubstituted or halogen-substituted alkenyl, alkinyl, alkenyloxy,alkenylthio or alkenylamino having in each case up to 6 carbon atoms inthe alkenyl or alkinyl groups, or represents unsubstituted orhalogen-substituted cycloalkyl, cycloalkylalkyl, cycloalkyloxy,cycloalkylthio or cycloalkylamino having in each case 3 to 6 carbonatoms in the cycloalkyl groups and optionally up to 4 carbon atoms inthe alkyl moiety, or represents unsubstituted or -halogen-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino,benzyl, benzyloxy, benzylthio or benzylamino, and R⁶ representshydrogen, hydroxyl, amino, alkylideneamino having up to 4 carbon atoms,or represents unsubstituted or halogen- or C₁-C₄-alkoxy-substitutedalkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in eachcase up to 6 carbon atoms in the alkyl groups, or representsunsubstituted or halogen-substituted alkenyl, alkinyl or alkenyloxyhaving in each case up to 6 carbon atoms in the alkenyl or alkinylgroups, or represents unsubstituted or halogen-substituted cycloalkyl,cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbonatoms in the cycloalkyl groups and optionally up to 3 carbon atoms inthe alkyl moiety, or represents unsubstituted or halogen-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted phenyl or benzyl, or together with anadjacent radical R⁵ or R⁶ represents unsubstituted or halogen- orC₁-C₄-alkyl-substituted alkanediyl having 3 to 5 carbon atoms, or—in thecase that two adjacent radicals R⁵ and R⁵ are located at a doublebond—together with the adjacent radical R⁵ also represents a benzogrouping.
 3. Substituted benzoylcyclohexanediones according to claim 1,wherein: m represents the numbers 0, 1 or 2, n represents the numbers 0,1 or 2, A represents a single bond, methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl), R¹ represents hydrogen, orrepresents unsubstituted or fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substitutedmethyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or representsmethoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, R² representsmethyl, ethyl, n- or i-propyl, or together with R¹ represents methylene,ethane-1,1-diyl (ethylidene, —CH(CH₃)—), ethane-1,2-diyl (dimethylene,—CH₂CH₂—), propane-1,3-diyl (trimethylene, —CH₂CH₂CH₂—), butane-1,4-diyl(tetramethylene, —CH₂CH₂CH₂CH₂—) or pentane-1,5-diyl (pentamethylene,—CH₂CH₂CH₂CH₂CH₂—), where in this case m represents 1 and R¹ and R² arelocated at the same carbon atom (“geminal”) or at two adjacent carbonatoms (“vicinal”), R³ represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or representsunsubstituted or fluorine- and/or chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethyl-sulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, or represents unsubstituted or fluorine- and/or chlorine-,methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- ori-propoxy, or represents unsubstituted or fluorine- and/orchlorine-substituted methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or representsmethylamino, ethylamino, n- or i-propylamino, dimethylamino,diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl, R⁴represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine,chlorine, bromine, or represents unsubstituted or fluorine-, chlorine-,fluorine and chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,methylthio-, ethylthio-, -n- or i-propylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or representsunsubstituted or fluorine-, chlorine-, fluorine and chlorine-, methoxy-,ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy,represents in each case optionally fluorine- and/or chlorine-substitutedmethylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino,dimethylaminosulphonyl or diethylaminosulphonyl, and Z represents one ofthe heterocyclic groupings below

in which the bond drawn broken in each case denotes a single bond or adouble bond, Q represents oxygen, R⁵ represents hydrogen, hydroxyl,mercapto, cyano, fluorine, chlorine, bromine, iodine, or representsunsubstituted or fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- ori-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-,ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-,ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-,i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, represents methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino,di-n-propylamino or di-i-propylamino, or represents unsubstituted orfluorine-, chlorine-, or fluorine and chlorine-substituted ethenyl,propenyl, butenenyl, ethinyl, propinyl, butinyl, propenyloxy,butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, orrepresents unsubstituted or fluorine-, chlorine-, or fluorine andchlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio,cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino orcyclohexylamino, or represents unsubstitued or fluorine-, chlorine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-,ethoxy-, n- or i-propoxy-substituted phenyl, phenyloxy, phenylthio,phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, and R⁶represents hydrogen, hydroxyl, amino, or represents unsubstituted orfluorine-, chlorine-, or fluorine and chlorine-, methoxy-, orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino ordimethylamino, or represents unsubstituted or fluorine-, chlorine-, orfluorine and chlorine-substituted ethenyl, propenyl, ethinyl, propinylor propenyloxy, or represents unsubstituted or fluorine-, chlorine-, orfluorine and chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, or represents unsubstituted or fluorine-, chlorine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-,ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, or together withan adjacent radical R⁵ or R⁶ represents unsubstituted or methyl- and/orethyl-substituted propane-1,3-diyl (trimethylene) or butane-1,4-diyl(tetramethylene), or—in the case that two adjacent radicals R⁵ and R⁵are located at a double bond—together with the adjacent radical R⁵ alsorepresents a benzo grouping.
 4. A method of controlling undesirableplants, comprising the step of applying one or more substitutedbenzoylcyclohexanediones according to claim 1 to undesirable plants ortheir habitats.
 5. A herbicidal composition comprising one or moresubstituted benzoylcyclohexanediones according to claim 1 and anextender.